Toluene → 4-(4-Dimethylaminophenylsulfanyl)-2-methylpent-2-en-1-ol
Reaction equation
C[O:2][C:3](=O)[C:4]([CH3:18])=[CH:5][CH:6]([S:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=1)[CH3:7].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>C1COCC1>[CH3:17][N:15]([CH3:16])[C:12]1[CH:13]=[CH:14][C:9]([S:8][CH:6]([CH3:7])[CH:5]=[C:4]([CH3:18])[CH2:3][OH:2])=[CH:10][CH:11]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-(4-dimethylaminophenylsulfanyl)-2-methylpent-2-enoic acid methyl ester (0.279 g, 1.0 mmol) in dry THF (4 mL) at 0° C. was added dropwise a solution of di-isobutylaluminium hydride in toluene (1M, 3.0 mL, 3.0 mmol), under an atmosphere of argon. After stirring at 0° C. for one hour (TLC monitoring), the mixture was quenched by addition of methanol (0.5 mL: CAUTION), then water (0.3 mL), 5% aqueous sodium hydroxide solution (0.3 mL) and lastly 30% aqueous sodium potassium tartrate (4 mL). The mixture was stirred for 2 hours at 20° C., then extracted with diethyl ether (3×10 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and evaporated to give the title compound (0.22 g, 88%) as a colourless oil.
Workup
- customthe mixture was quenched by addition of methanol (0.5 mL: CAUTION)
- stirringThe mixture was stirred for 2 hours at 20° C.
- extractionextracted with diethyl ether (3×10 mL)
- dry with materialThe combined organic layers were dried over anhydrous MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-ec9bfa5c612143cd99f27e6e868d2997
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07683185B2
Reaction notes
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