Water → HCID 13417327, compound

HRID 1284478Notes

Reaction equation

HRID 1284478 reaction equation
[C:1]1(/[C:7](/[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.O>C(Cl)Cl>[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([O-:14])(=[O:35])=[O:34])=[CH:29][CH:28]=1.[C:1]1(/[C:7](/[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 13417327HCID 13417327, compound

Product 2

HCID 85570p-ToluenesulfonateHCID 13417327HCID 13417327, compoundYield 274%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-7-Phenyl-7-(3-pyridyl)-6-hepten-1-ol (2.3 g, 8.6 mmoles) was dissolved in methylene chloride (2.0 ml), and pyridine (1 ml) and p-toluenesulfonyl chloride (1.8 g, 9.4 mmoles) were added. The reaction was allowed to proceed at room temperature overnight, and water (30 ml) was added, followed by extraction of the product with ethyl acetate. The organic layer was washed with water and dried and the solvent was distilled off. The resulting oily product was subjected to silica gel column chromatography using isopropyl ether-ethyl acetate (1:1) as the eluent to give p-toluensulfonate of (E)-7-phenyl-7-(3-pyridyl)-6-hepten-1-ol (3.15 g, 88%) as an oil.

Workup

  1. extractionfollowed by extraction of the product with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-8503d9a7ac3d4d15a5087a758f2ab753
Source dataset
uspto-grants-1986_01
Patent number
US04563446

Reaction notes

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