Diazomethane → Methyl 5-methyl-4-hexenoate

HRID 2293894Notes

Reaction equation

HRID 2293894 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-a6f53a5e5fca4cf1be9c47f0feb06c6f
Source dataset
uspto-grants-1997_11
Patent number
US05688487

Reaction notes

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