Acetic Acid → HCID 14262258, compound

HRID 2231234Notes

Reaction equation

HRID 2231234 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH:13]([N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[CH:16]1)=[CH2:14].[CH:24](OCC)=[O:25].C(O)(=O)C>CCCCCC.O1CCCC1.C(OCC)(=O)C.O>[CH:13]([N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[CH:24]=[O:25])=[CH2:14]

Participants

10

Reactant 5

HCID 176Acetic AcidHCID 7912DiisopropylamineHCID 8025Ethyl formateHCID 588994HCID 588994, compoundHCID 178418339Butyllithium

Product 1

HCID 14262258HCID 14262258, compoundYield 41.1%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold (-78° C.) solution of dry tetrahydrofuran (300 ml) containing 13.27 ml (94.6 mmoles) of diisopropylamine was added 37.86 ml of 2.5M solution of n-butyl lithium in hexane and the mixture stirred for 30 minutes. 1-Vinylbenzimidazole (13.6 g, 94.6 mmoles) in 50 ml of tetrahydrofuran was added and the mixture stirred for 30 minutes. Ethyl formate (8.4 ml, 104.1 mmoles) was then added and the reaction mixture stirred, allowing to warm to room temperature, overnight. Acetic acid (5.4 ml, 99.6 mmoles) was added and the reaction added to 500 ml of water and 300 ml of ethyl acetate. The organic layer was separated, the water layer extracted with additional ethyl acetate (2×100 ml), and the organic phases combined, dried over magnesium sulfate and concentrated to an oil, 17 g. The residue was purified by chromatographing on 700 g of silica gel using ethyl acetate-chloroform (1:9; v:v) as the eluent to give 6.7 g of product as a light brown solid.

Workup

  1. stirringthe mixture stirred for 30 minutes
  2. stirringthe reaction mixture stirred
  3. customThe organic layer was separated
  4. extractionthe water layer extracted with additional ethyl acetate (2×100 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to an oil, 17 g
  7. customThe residue was purified by chromatographing on 700 g of silica gel

Sources & evidence

ORD record
ord-fc9b276a8ae1491a96839ffdd97399cf
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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