Dichloromethane → 4-(2-Fluorophenyl)-3-hydroxy-2-methylbutyl tosylate
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:15])(O)[CH:10]([CH3:13])[CH2:11][OH:12].C(N(CC)CC)C.ClCCl.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>O>[S:32]([C:29]1[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=1)([O:12][CH2:11][CH:10]([CH3:13])[CH:9]([OH:15])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])(=[O:34])=[O:33]Participants
6
Procedure
Under a nitrogen atmosphere, a mixture of 13.5 g (68.1 mmol) of 4-(2-fluorophenyl)-3-hydroxy-2-methylbutane-1,3-diol, 14.2 ml (21.3 mmol) of triethylamine, and 70 ml of dichloromethane was cooled with an ice bath and 13.0 g (68.1 mmol) of p-toluenesufonyl chloride was added to the mixture. After stirring overnight at room temperature, 100 ml of water was added thereto, followed by extraction 3 times each with 200 ml of dichloromethane, and the combined organic layer was dried with anhydrous sodium sulfate. After drying, the solvent was distilled off and the residue was purified by silica gel column chromatography to obtain 21.1 g of the title compound as a colorless oil. (Yield: 88%)
Workup
- temperaturewas cooled with an ice bath
- extractionfollowed by extraction 3 times each with 200 ml of dichloromethane
- dry with materialthe combined organic layer was dried with anhydrous sodium sulfate
- customAfter drying
- distillationthe solvent was distilled off
- customthe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-4e56efa2cda5482fb900e092ba09a00d
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06717016B2
Reaction notes
Loading…