2-Chloro-N-methoxy-N-methylacetamide → (S)-2-chloro-1-(2-methyloxy-3-(1-methyloxyheptyl)phenyl)ethanone

HRID 41530Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C@@H:8]([O:15][CH3:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:3]=1[O:17][CH3:18].CON(C)[C:22](=[O:25])[CH2:23][Cl:24]>C1COCC1>[Cl:24][CH2:23][C:22]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C@@H:8]([O:15][CH3:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:3]=1[O:17][CH3:18])=[O:25]

Participants

Conditions

Temperature: 45 °C

Procedure

To a THF solution of (S)-1-bromo-2-methyloxy-3-(1-methyloxyheptyl)benzene (9, 12.5 g) obtained in the second step was added dropwise a 2M isopropyl magnesium chloride THF solution (44 mL) under ice-cooling. After the reaction solution was stirred at 45° C. for 3 hours, N-methyloxy-N-methyl-2-chloroacetamide (10, 3.5 g) was added under ice-cooling, and the mixture was stirred at room temperature for 1 hour. The reaction solution was extracted with ethyl acetate, and purified by silica gel chromatography to obtain (S)-2-chloro-1-(2-methyloxy-3-(1-methyloxyheptyl)phenyl)ethanone (11).

Workup

temperaturecooling
temperaturecooling
stirringthe mixture was stirred at room temperature for 1 hour
extractionThe reaction solution was extracted with ethyl acetate
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-ec9e16da43be4014a0025b0506e220ba
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530668B2

Reaction notes

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