Methanol → (E)-3-Cyclohexyl-2-(4-methanesulfonyl-phenyl)-prop-2-en-1-ol
Reaction equation
CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C([O:19][C:20](=O)/[C:21](/[C:29]1[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1)=[CH:22]/[CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)C.CO>C1COCC1.O.C(OCC)(=O)C>[CH:23]1(/[CH:22]=[C:21](\[C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=2)/[CH2:20][OH:19])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -78 °C
Procedure
Add a solution of DIBAL in toluene (36.5 mL, 1.5 M, 54.6 mmol) dropwise over one h to a solution of (E)-3-cyclohexyl-2-(4-methanesulfonyl-phenyl)-acrylic acid ethyl ester (7.35 g, 21.8 mmol) in THF (200 mL) cooled to −78° C. Then allow the reaction mixture to slowly warm to r.t., and stir it for 18 h. Add methanol (50 mL), and then remove volatiles under vacuum. Partion the residue between ethly acetate (200 mL) and water (200 mL). Then extract the aqueous layer with ethyl acetate (2×300 mL). Combine the organic layers, wash them with saturated aqueous sodium chloride solution (200 mL), dry them over magnesium sulfate, and then filter them through celite®. Concentrate the filtrate to afford the title compound as an oil (6.0 g). MS (m/e): 295 (M+H).
Workup
- temperatureto slowly warm to r.t.
- extractionThen extract the aqueous layer with ethyl acetate (2×300 mL)
- washCombine the organic layers, wash them with saturated aqueous sodium chloride solution (200 mL)
- dry with materialdry them over magnesium sulfate
- filtrationfilter them through celite®
- concentrationConcentrate the filtrate
Sources & evidence
- ORD record
- ord-2ad62b2f25714f709fc633413617f5fc
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576108B2
Reaction notes
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