Water → HCID 23047799, compound

HRID 2107143Notes

Reaction equation

HRID 2107143 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]Br)=[CH:6][CH:5]=1.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:24])=[CH:19][CH:18]=1.O>CS(C)=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:25]([S:23]([C:20]2[CH:19]=[CH:18][C:17]([CH3:16])=[CH:22][CH:21]=2)=[O:24])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10753909HCID 10753909, compoundHCID 13068871HCID 13068871, compound

Product 1

HCID 23047799HCID 23047799, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

First 1.64 g (37.6 mmol) of sodium hydride in 55% mineral oil suspension, and then 9.8 g (37.6 mmol) of 5-(4-chlorophenyl)pentyl bromide, are added to a solution of 8.5 g (37.6 mmol) of ethyl 4-methylphenylsulfinylacetate in 75 ml of dimethylsulfoxide. Then the mixture is stirred at room temperature for another 4 hours. Then it is poured into water, extracted with ether, the extracts are washed with water, dried and concentrated. The concentrate is chromatographed with a mixture of n-heptane and butanone (2:1) on silica gel. Yield: 8.0 g (52% of theory) of ethyl 7-(4-chlorophenyl)-2-[(4-methylphenyl)sulfinyl]heptanoate, a colorless oil.

Workup

  1. extractionextracted with ether
  2. washthe extracts are washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe concentrate is chromatographed with a mixture of n-heptane and butanone (2:1) on silica gel

Sources & evidence

ORD record
ord-70b0a8dc98ec45c68fe0ac42453f566e
Source dataset
uspto-grants-1990_06
Patent number
US04933367

Reaction notes

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