Ethyl Acetate → Ethyl 4-(m-methoxyphenyl)-3-phenyl-3-hydroxybutyrate
Reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].[C:11]([O:14][CH2:15][CH3:16])(=[O:13])[CH3:12].[C:17]1([C:23]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=2)=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[CH3:33][O:32][C:28]1[CH:27]=[C:26]([CH2:25][C:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([OH:24])[CH2:12][C:11]([O:14][CH2:15][CH3:16])=[O:13])[CH:31]=[CH:30][CH:29]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
Lithium hexamethyldisilazane (88.5 mL, 88.5 mmol) was added to THF (150 mL) at −78° C. After 15 min, ethyl acetate (7.79 g, 88.5 mmol) was added over 10 min and stirred at −78° C. for 30 min. The m-methoxybenzyl phenyl ketone in (10.0 g, 44.25 mmol) THF (100 mL) was added over 15 min and kept at that temperature for 3 h. The reaction mixture was quenched at that temperature with saturated ammonium chloride (15 mL). The reaction mixture was diluted with ether (200 mL) and the organic layer was washed with brine, (100 mL), dried and was concentrated to afford 12 g (86%) of the desired product. 1H NMR (CDCl3) δ 7.10-7.37 (m, 6H), 6.71-6.74 (m, 1 H), 6.60-6.62 (m, 1 H), 6.48 (s, 1 H), 3.95-4.00 (m, 2H), 3.67 (s, 3H), 2.72-3.07 (m, 4H), 1.06 (m, 3H).
Workup
- waitkept at that temperature for 3 h
- customThe reaction mixture was quenched at that temperature with saturated ammonium chloride (15 mL)
- additionThe reaction mixture was diluted with ether (200 mL)
- washthe organic layer was washed with brine, (100 mL)
- customdried
- concentrationwas concentrated
Sources & evidence
- ORD record
- ord-c89c9eece0954ccb90a04a581a9fe930
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06833366B1
Reaction notes
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