Diazomethane → Methyl 5-methyl-4-hexenoate

HRID 278381

Reaction equation

HRID 278381 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-8719e9fbf4f148e0868d240a4d0102b4
Source dataset
uspto-grants-2002_03
Patent number
US06359120B1

Linked notes

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