Water → alpha-(5-Bromopentyl)-alpha-(cyclohexylthio)-3,4-dimethoxybenzeneacetonitrile

HRID 1078789Notes

Reaction equation

HRID 1078789 reaction equation
[CH:1]1([S:7][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[C:9]#[N:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br.O>O1CCCC1>[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:8]([S:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[C:9]#[N:10]

Participants

6

Reactant 4

HCID 962WaterHCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 10541608alpha-(Cyclohexylthio)-3,4-dimethoxybenzeneacetonitrile

Product 1

HCID 19042070alpha-(5-Bromopentyl)-alpha-(cyclohexylthio)-3,4-dimethoxybenzeneacetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7.57 g of product from Example 82 in 180 ml of anhydrous tetrahydrofuran, under argon, is added 1.3 g of 50% sodium hydride in oil. The mixture is stirred at room temperature for 1 hour; followed by the addition of 10.6 ml of 1,5-dibromopentane and the stirring is continued for 4 hours at room temperature. The reaction mixture is poured into 450 ml of water and extracted with diethyl ether. The organic layer is washed with saturated sodium chloride, dried, filtered and concentrated in vacuo to give 23 g of a crude oil. The oil is purified by chromatography (silica gel: hexane to 10% ethyl acetate/hexane) to give 8.9 g of the desired product.

Workup

  1. waitthe stirring is continued for 4 hours at room temperature
  2. extractionextracted with diethyl ether
  3. washThe organic layer is washed with saturated sodium chloride
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give 23 g of a crude oil
  8. customThe oil is purified by chromatography (silica gel: hexane to 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-52cf378c6b9a406d8ed8ca6640e73454
Source dataset
uspto-grants-1996_08
Patent number
US05550149

Reaction notes

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