Diisopropylamine → HCID 86734327, compound

HRID 236706Notes

Reaction equation

HRID 236706 reaction equation
C([Li])C[CH2:3][CH3:4].C(N[CH:10]([CH3:12])[CH3:11])(C)C.[CH3:13][O:14][C:15](=[O:19])C(C)C.[CH:20]([C:22](CC)=[O:23])=C>CCCCCC.O1CCCC1>[CH3:13][O:14][C:15](=[O:19])[C:10]([CH3:11])([CH3:12])[CH:20]=[CH:22][O:23][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 11039Methyl isobutyrateHCID 153941-Penten-3-oneHCID 178418339Butyllithium

Product 1

HCID 86734327HCID 86734327, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of n-butyllithium in hexane (224 ml; 2.2 M) was added to tetrahydrofuran (THF, 300 ml) at -60° followed by diisopropylamine (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-bf878590abc8457f82122a5c670ad090
Source dataset
uspto-grants-1979_06
Patent number
US04157345

Reaction notes

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