Diazomethane → Methyl 5-methyl-4-hexenoate

HRID 47160

Reaction equation

HRID 47160 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) δ1.62 & 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-32ee0f1e9343437cab24338b7c57f84b
Source dataset
uspto-grants-2004_03
Patent number
US06699458B2

Linked notes

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