Methyl isobutyrate → 2,2-Dimethyl-5-oxoheptenoic acid methyl ester

HRID 442403Notes

Reaction equation

HRID 442403 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8](=[O:12])[CH:9]([CH3:11])[CH3:10].[CH:13]([C:15]([CH2:17][CH3:18])=[O:16])=[CH2:14]>CCCCCC.O1CCCC1>[CH3:6][O:7][C:8](=[O:12])[C:9]([CH3:11])([CH3:10])[CH:14]=[CH:13][C:15](=[O:16])[CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 11039Methyl isobutyrateHCID 153941-Penten-3-oneHCID 178418339Butyllithium

Product 1

HCID 542613512,2-Dimethyl-5-oxoheptenoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of n-butyllithium in hexane (224 ml; 2.2M) was added to tetrahydrofuran (THF, 300 ml) at -60° followed by diiospropylamine (52 g) and this mixture was then warmed to room temperature stirred for 5 min and then cooled to -72° C. Methylisobutyrate (50 g) was then slowly added and the mixture was stirred for 11/2 hr at -70° C. Freshly distilled ethyl vinyl ketone (42 g) in THF (60 ml) was added to the above mixture over 10 min and the mixture was then stirred for a further one half hr at -60° C and subsequently at room temperature for 2 hr.

Workup

  1. temperaturecooled to -72° C
  2. stirringthe mixture was stirred for 11/2 hr at -70° C
  3. stirringthe mixture was then stirred for a further one half hr at -60° C and subsequently at room temperature for 2 hr

Sources & evidence

ORD record
ord-440c591f4d934efe82ae51e8a270c7db
Source dataset
uspto-grants-1977_08
Patent number
US04045476

Reaction notes

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