Diazomethane → Methyl 5-methyl-4-hexenoate

HRID 634893

Reaction equation

HRID 634893 reaction equation
[N+](=[CH2:3])=[N-].[CH3:4][C:5]([CH3:12])=[CH:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]>CCOCC>[CH3:4][C:5]([CH3:12])=[CH:6][CH2:7][CH2:8][C:9]([O:11][CH3:3])=[O:10]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 124253245-Methyl-4-hexenoic acid

Product 1

HCID 10909672Methyl 5-methyl-4-hexenoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Freshly prepared diazomethane in ether was added to an ice-cooled solution of 5-methyl-4-hexenoic acid (4.5 g, 35.16 mmol) in ether (10 mL) until the solution became slightly yellow in color. The solvent was then evaporated under vacuum to afford the title product as a colorless liquid in near quantitative yield (4.90 g). This product was used in the next reaction step without further purification. 1H NMR (CDCl3) δ 1.62 & 1.68 [2s, 6H, C(CH3)2], 2.30 [m, 4H, (CH2)2], 3.69 (s, 3H, COOCH3) and 5.07 (t, 1H, CH).

Workup

  1. customThe solvent was then evaporated under vacuum

Sources & evidence

ORD record
ord-5c67a1c71013403db9338d06be7ae993
Source dataset
uspto-grants-2001_02
Patent number
US06184361B2

Linked notes

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