Water → HCID 15617940, compound

HRID 703919Notes

Reaction equation

HRID 703919 reaction equation
[CH2:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[OH:14])[CH:2]=[CH2:3].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.[OH2:26]>N1C=CC=CC=1>[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21]([O:26][CH2:3][CH2:2][CH2:1][C:4]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[O:14][CH2:1][C:4]2[CH:13]=[CH:12][CH:11]=[CH:6][CH:5]=2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 10655090HCID 10655090, compound

Product 1

HCID 15617940HCID 15617940, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of the product of Example 118 Part C (9.10 g, 0.031 mole) in pyridine (150 mL) was stirred at 0° and treated with p-toluenesulfonyl chloride (6.70 g, 0.035 mole), then stirred for 16 hours at room temperature. The solution was poured into water, and the mixture extracted with ethyl acetate. The resulting oil was chromatographed with 4:1 hexane/ether to provide the title compound (3.20 g, 23%) as an oil.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. customThe resulting oil was chromatographed with 4:1 hexane/ether

Sources & evidence

ORD record
ord-dd4b4104bb2f41e9be04774c3d4cd5d0
Source dataset
uspto-grants-1991_01
Patent number
US04985435

Reaction notes

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