Trimethylsilyldiazomethane → Methyl 2-(4-fluorophenyl)-2-oxoacetate

HRID 2229479Notes

Reaction equation

HRID 2229479 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:13][Si](C=[N+]=[N-])(C)C.CCCCCC.CCOCC>C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:12])[C:9]([O:11][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 167693TrimethylsilyldiazomethaneHCID 5794402-(4-Fluorophenyl)-2-oxoacetic AcidHCID 21584099Diethylether hexane

Product 1

HCID 10965144Methyl 2-(4-fluorophenyl)-2-oxoacetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-fluorophenyl glyoxylic acid (100 mg, 0.595 mmol) in ethyl ether (5 ml) was added trimethylsilyl diazomethane (2 M/hexane, 1 ml) at 0° C. TLC showed reaction was complete after 1 h. The ether was evaporated to leave a yellow oil. Chromatography with hexane/ether (95:5) gave methyl 4-fluorophenylglyoxalate as a pale yellow oil (75 mg). 500 MHz 13C NMR (CDCl3): δ 184.11; 167.85; 165.79; 163.59; 133.04; 132.96; 128.97; 116.33; 116.16; 115.90; 115.72; 52.85.

Workup

  1. customreaction
  2. customThe ether was evaporated
  3. customto leave a yellow oil

Sources & evidence

ORD record
ord-e62bb20f46c34ecaae120fbc72883c9e
Source dataset
uspto-grants-2002_07
Patent number
US06420418B1

Reaction notes

Loading…