Hexane → HCID 86734327, compound

HRID 371972Notes

Reaction equation

HRID 371972 reaction equation
C([Li])C[CH2:3][CH3:4].[CH3:6][O:7][C:8](=[O:12])[CH:9]([CH3:11])[CH3:10].C([C:15](CC)=[O:16])=C.[CH3:19]CCCCC>O1CCCC1>[CH3:6][O:7][C:8](=[O:12])[C:9]([CH3:19])([CH3:11])[CH:10]=[CH:15][O:16][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 8058HexaneHCID 11039Methyl isobutyrateHCID 153941-Penten-3-oneHCID 178418339Butyllithium

Product 1

HCID 86734327HCID 86734327, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 1/2 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 1/2 hr at -60° C and subsequently at room temperature for 2 hr

Sources & evidence

ORD record
ord-1a6dff17e5e746ee9985b90dbf882d0b
Source dataset
uspto-grants-1978_05
Patent number
US04088689

Reaction notes

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