Dimethylformamide → HCID 76579095, compound

HRID 730973Notes

Reaction equation

HRID 730973 reaction equation
[CH2:1]([C:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=[CH:4][CH3:5])[CH3:2].[Li]CCCC.CN([CH:21]=[O:22])C>C1COCC1>[CH2:4]([C:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([CH:7]=1)[CH:21]=[O:22])=[CH:1][CH3:2])[CH3:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67271716HCID 67271716, compoundHCID 178418339Butyllithium

Product 1

HCID 76579095HCID 76579095, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(1-ethyl-propenyl)-4-fluoro-benzene (15.3 g, 93.2 mmol) in THF (150 mL) at −78° C. is treated with n-BuLi (70 mL, 1.6 M). The reaction mixture is allowed to warm to 0° C. over 60 min, cooled to −78° C., and treated with DMF (10.2 g, 140 mmol). The mixture is stirred for 10 min and quenched with HOAc (10 mL) and water (200 mL). The mixture is allowed to warm to RT, and the THF is removed under vacuum. The residue is extracted with EtOAc (2×100 mL, and the organic layer is dried over Na2SO4 andconcentrated. The crude product is purified using silica gel column chromatography (7% EtOAc/Hex) to afford the title compound (8.70 g, 49%).

Workup

  1. temperaturecooled to −78° C.
  2. customquenched with HOAc (10 mL) and water (200 mL)
  3. temperatureto warm to RT
  4. customthe THF is removed under vacuum
  5. extractionThe residue is extracted with EtOAc (2×100 mL
  6. dry with materialthe organic layer is dried over Na2SO4
  7. customThe crude product is purified

Sources & evidence

ORD record
ord-332676bd01ed4a019ffa6c517ff1ead3
Source dataset
uspto-grants-2009_09
Patent number
US07582775B2

Reaction notes

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