Hydrochloric Acid → Methyl 3-(2-methoxyphenyl)-3-oxopropanoate

HRID 610112Notes

Reaction equation

C[Si](N[Si](C)(C)C)(C)C.[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][C:16](OC)=[CH:15][CH:14]=1)=[O:12].[CH3:21][O:22][C:23](=[O:26])OC.Cl.C1C[O:31][CH2:30]C1>CCOC(C)=O>[CH3:21][O:22][C:23](=[O:26])[CH2:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=1[O:31][CH3:30])=[O:12]

Participants

Conditions

Temperature: -78 °C

Procedure

Bis-(trimethylsilyl)amine (158.2 mL, 0.750 mol) was dissolved in 150 mL of THF and cooled to -78° C. with the aid of a dry ice/acetone bath. N-butyl lithium (2.5 M in hexane, 300 mL, 0.750 mol) was introduced via cannula into the system and stirred at that temperature for 20 min. 4-methoxy acetophenone (51.20 g, 0.340 mol) was added via a solid addition funnel and stirred at -78° C. for 3 h. Dimethylcarbonate (87.0 mL, 1.02 mol) was added via cannula and the system allowed to stir overnight with warming to room temperature. The solution was acidified with 10% HCl, diluted with 1 liter of EtOAc and washed three times with 400 mL of 10% HCl. The organics were dried over MgSO4, filtered through a silica gel plug and the volatiles removed in vacuum. The title compound was obtained as a viscous brown oil (65.09 g, 91.7%) MS (NH3 -DCI) 347.9 (M+H)+.

Workup

stirringstirred at -78° C. for 3 h
stirringto stir overnight
temperaturewith warming to room temperature
washwashed three times with 400 mL of 10% HCl
dry with materialThe organics were dried over MgSO4
filtrationfiltered through a silica gel plug
customthe volatiles removed in vacuum

Sources & evidence

ORD record: ord-3854a1972d134a06a773d7631c682ef3
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998424

Reaction notes

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