Trimethylsilyldiazomethane → Methyl 3-acetylbenzoate

HRID 714457Notes

Reaction equation

HRID 714457 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].[CH3:13][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO.C(OCC)C>[C:1]([C:4]1[CH:5]=[C:6]([C:7]([O:9][CH3:13])=[O:8])[CH:10]=[CH:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 2203243-Acetylbenzoic acid

Product 1

HCID 15094405Methyl 3-acetylbenzoate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

3.95 g (24.06 mmol) of 3-acetylbenzoic acid were initially charged in 100 ml of toluene and 75 ml of methanol. After dropwise addition of 4.12 g (36.09 mmol) of trimethylsilyldiazomethane 2M in diethyl ether at RT, an instant evolution of gas in the reaction solution was observed. Another 0.27 g (2.4 mmol) of trimethylsilyldiazomethane 2M in diethyl ether was added until the reaction solution remained yellow, and the mixture was stirred at RT for 10 min. The reaction solution was evaporated.

Workup

  1. customThe reaction solution was evaporated

Sources & evidence

ORD record
ord-a4185f0c5e674338ac906d2a2b68008f
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

Loading…