Methyl propionate → 3-(4-Benzyloxy-phenyl)-3-hydroxy-2-methyl-propionic acid methyl ester

HRID 2212564Notes

Reaction equation

[Li+].CC([N-]C(C)C)C.[C:9]([O:13][CH3:14])(=[O:12])[CH2:10][CH3:11].[CH2:15]([O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[CH3:14][O:13][C:9](=[O:12])[CH:10]([CH3:11])[CH:27]([C:26]1[CH:25]=[CH:24][C:23]([O:22][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:30][CH:29]=1)[OH:28]

Participants

Conditions

Temperature: -78 °C

Procedure

LDA (1.3 mL, 2.6 mmol) was added to a solution of methyl propionate (0.22 g, 2.6 mmol) in THF (5 mL) cooled to −78° C. under nitrogen atmosphere. The reaction was stirred for 30 min, and then 4-benzyloxy-benzaldehyde (0.50 g, 2.4 mmol) in THF (5 mL) was added. The reaction was stirred at −78° C. for 5 min, and then allowed to warm to room temperature and stirred overnight. The reaction was partitioned between ethyl acetate and 1N HCl. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by FCC on silica gel eluting ethyl acetate:hexane (15:85 to 25:75) gradient to give 3-(4-benzyloxy-phenyl)-3-hydroxy-2-methyl-propionic acid methyl ester (0.12 g, 16%) as an oil. MS found: (M+H)+=301.

Workup

stirringThe reaction was stirred at −78° C. for 5 min
temperatureto warm to room temperature
stirringstirred overnight
customThe reaction was partitioned between ethyl acetate and 1N HCl
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customto give an oil
customThe product was purified by FCC on silica gel
washeluting ethyl acetate:hexane (15:85 to 25:75) gradient

Sources & evidence

ORD record: ord-072008b61daa4363a2fcf32792939a98
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07102008B2

Reaction notes

Loading…