Diisopropylamine → HCID 10987849, compound

HRID 2058131Notes

Reaction equation

HRID 2058131 reaction equation
C([N-][CH:5]([CH3:7])[CH3:6])(C)C.[Li+].[CH2:9]([Li])[CH2:10][CH2:11][CH3:12].C(NC(C)C)(C)C.[C:21]([O:24][CH2:25][CH3:26])(=[O:23])C.O1[CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH3:12]/[C:11](=[CH:7]\[CH2:5][CH2:6][C:29](=[CH2:28])[CH:30]=[CH2:31])/[CH2:10][CH2:9][C:21]([O:24][CH2:25][CH3:26])=[O:23]

Participants

6

Reactant 5

HCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 10987849HCID 10987849, compoundYield 70%

Conditions

Temperature
0 °C

Procedure

Lithium diisopropylamide (15 mM) is generated from n-butyl lithium and diisopropylamine in tetrahydrofuran (100 ml) in the usual manner. Ethyl acetate (1.3 g, 14.6 mM) is added to this reagent at -78° C. under nitrogen and the mixture is stirred for two hours. A solution of 1-chloro-2-methyl-6-methylene-2(E)-7-octadiene (2.5 g, 14.6 mM) in tetrahydrofuran (3 ml) is added dropwise during a ten minute period. The resultant mixture is stirred for two hours and then allowed to warm to 0° C., after which ice-water is added (50 ml). The aqueous phase is washed with brine (100 ml), water (2×100 ml) and then dried (Na2SO4). The solvent is removed in vacuo to give a crude product (2.9 g). This material is further purified by column chromatography on silica gel (50 g) with 10% ether in petroleum to give ethyl 4-methyl-8-methylene-(E)-4,9-decadienoate (2.1 g, 70%) as a colorless liquid.

Workup

  1. washThe aqueous phase is washed with brine (100 ml), water (2×100 ml)
  2. dry with materialdried (Na2SO4)
  3. customThe solvent is removed in vacuo
  4. customto give a crude product (2.9 g)
  5. customThis material is further purified by column chromatography on silica gel (50 g) with 10% ether in petroleum

Sources & evidence

ORD record
ord-a29d9b8772d245539eec494796095cbb
Source dataset
uspto-grants-1980_07
Patent number
US04215048

Reaction notes

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