1-Tetradecanol → Tetradecyl 2-(2,2-difluorocyclopropyl)acetate
Reaction equation
[CH2:1]([OH:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(N(CC)CC)C.[F:23][C:24]1([F:31])[CH2:26][CH:25]1[CH2:27][C:28](Cl)=[O:29]>O1CCCC1.CN(C)C1C=CN=CC=1>[F:23][C:24]1([F:31])[CH2:26][CH:25]1[CH2:27][C:28]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:29]Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2.08 g (9.7 mmol) 1-tetradecanol in 20 ml tetrahydrofuran (THF) was treated with 200 mg 4-dimethylaminopyridine (DMAP) and 1.35 ml (9.7 mmol) triethylamine and cooled to 0° C. A solution of 1.5 g (9.7 mmol) 2-(2,2-difluorocyclopropyl)acetyl chloride in 10 ml tetrahydrofuran at 0°-5° C. was added dropwise. The mixture was then stirred for 2 hours at room temperature. The precipitated triethylamine hydrochloride was separated, the solution concentrated under reduced pressure, and the residue dissolved in 50 ml diethyl ether. After washing with in turn 10 ml water, 10% caustic soda and water until neutral, the ether solution was dried over magnesium sulphate and evaporated in vacuo (200 mbar). The residue was distilled under an oil pump vacuum.
Workup
- customThe precipitated triethylamine hydrochloride was separated
- concentrationthe solution concentrated under reduced pressure
- dissolutionthe residue dissolved in 50 ml diethyl ether
- washAfter washing with in turn 10 ml water, 10% caustic soda and water until neutral, the ether solution
- dry with materialwas dried over magnesium sulphate
- customevaporated in vacuo (200 mbar)
- distillationThe residue was distilled under an oil pump vacuum
Sources & evidence
- ORD record
- ord-0becca1fffc7429988d60b0a663e7a12
- Source dataset
- uspto-grants-1992_02
- Patent number
- US05089662
Reaction notes
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