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Synthetic method for fluoromethylation of alcohols
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A technology of fluoromethylation and halohydrin, which is applied in the field of fluoromethylation of halohydrin, and can solve problems such as expensive, low yield of fluorinated products, and influence on reversible regulation
Inactive Publication Date: 2005-06-08
ABBOTT LAB INC
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Although the exact mechanism of action of sevoflurane has not yet been elucidated, it has recently been found that sevoflurane interacts with nicotinic acetylcholine receptors by affecting the open and closed states of ion channels at critical or lower concentrations
Sevoflurane may also affect reversible regulation of GABA and glycine receptors
[0011] While the methods described above can be used to prepare some fluorides, these methods can be complex, expensive, and often yield low yields of fluorinated products with considerable by-products
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Embodiment 1
[0037] According to Reaction Scheme I, methoxy-1,1,1,3,3,3-hexafluoroisopropoxymethane was synthesized in the following manner.
[0042] Add ice-cold and well-stirred ZnCl for 5 minutes 2 (41 g, 0.30 mol) in 1,1,1,3,3,3-hexafluoroisopropanol (31.5 mL, 0.31 mol) was slowly added dimethoxymethane (24 mL, 0.30 mol). The reaction mixture was allowed to warm to room temperature over 1 hour, then heated at reflux. After reflux for 6 hours, the contents of the reaction flask were distilled, leaving a solid residue in the flask. The distillate was washed with 2N NaOH (10×4), water (10 mL), brine (10 mL), the bottom organic layer was separated and dried over anhydroussodiumsulfate, filtered to give methoxy-1,1,1,3 , 3,3-Hexafluoroisopropoxymethane (34 g, 55%).
Embodiment 2
[0044] According to Reaction Scheme II, sevoflurane was synthesized in the following manner.
[0050] To methoxy-1,1,1,3,3,3-hexafluoroisopropoxymethane (3.57 g, 17 mmol) was added anhydrous AlCl at room temperature 3 (2.25 g, 17 mmol), then the reaction flask was heated at 95°C. After 14 hours, the reaction mixture was cooled to room temperature, then PEG-400 (5.0 mL) and KF (1.97 g, 34 mmol) were added. The reaction mixture was then reheated to 95°C. After 18 hours, the reaction mixture was cooled to room temperature and diluted with 20 mL of water. The lower organic layer was separated and distilled to give sevoflurane (2.4 g, 51%).
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Abstract
The present invention relates to a method for fluoromethylation of haloalcohols. The method includes providing the formula R 1 C(CX 3 ) 2 The α-halohydrin step of OH, where R 1 selected from hydrogen, alkyl. The α-halohydrin and the chemical formula are CH 2 (OR 2 ) 2 The first compound reacts in the presence of an acid catalyst to form an acetal. The resulting acetal is chlorinated with a chlorinating agent to form the formula R 1 C(CX 3 ) 2 OCH 2 Chloride of Cl. The chloride is then converted to the chemical formula R with a fluorinating agent 1 C(CX 3 ) 2 OCH 2 Fluoride of F.
Description
field of invention [0001] The invention relates to a method for fluoromethylation of haloalcohols. Alcohols are reacted with dialkoxymethane under acidic conditions to give acetals which are then fluorinated by reaction with Lewis acids and fluorinating agents. The process yields high fluoride and can be performed in a single vessel. Preferably this method is used for the synthesis of sevoflurane from hexafluoroisopropanol. Background of the invention [0002] Anesthetics are biochemical sedatives that affect the vital functions of cells. Anesthetics generally produce analgesia, loss of consciousness, decreased reflex activity, and muscle relaxation with minimal suppression of vital functions. Anesthetics can be gaseous (volatile) or solidified (nonvolatile). Gaseous anesthetics are inhaled and passed through the lungs into the bloodstream, while coagulated anesthetics are administered parenterally or through the digestive tract. [0003] Many gaseous anesthetics in cur...
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