Trimethylsilyldiazomethane → Methyl 3-oxocyclobutane-1-carboxylate

HRID 1508477Notes

Reaction equation

HRID 1508477 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[O:8]=[C:9]1[CH2:12][CH:11]([C:13]([OH:15])=[O:14])[CH2:10]1>CO.C(Cl)Cl>[O:8]=[C:9]1[CH2:12][CH:11]([C:13]([O:15][CH3:1])=[O:14])[CH2:10]1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 13992367Methyl 3-oxocyclobutane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Trimethylsilyldiazomethane (21.0 mL of a 2 M solution in hexanes, 42.1 mmol) was added to a stirred solution of 3-oxocyclobutanecarboxylic acid (3.00 g, 26.3 mmol) in dry MeOH (11.1 mL) and dry CH2Cl2 (100 mL) at 25° C. under N2. The reaction was stirred at 25° C. for 2 h. The reaction mixture was concentrated in vacuo to afford methyl 3-oxocyclobutanecarboxylate, as an oil. 1H NMR (500 MHz, CHCl3): δ 3.75 (s, 3H); 3.44-3.37 (m, 2H); 3.31-3.17 (m, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-501cc021a293482fa6495a66ebcc2fbb
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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