4-Toluenesulfonyl chloride → HCID 19786608, compound

HRID 1657105Notes

Reaction equation

HRID 1657105 reaction equation
[OH:1][CH:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][O:10][C:6]=2[CH2:5][CH2:4][CH:3]1[CH2:17][CH2:18][OH:19].[S:20](Cl)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>N1C=CC=CC=1>[C:11]1([C:8]2[C:7]3[CH:2]([OH:1])[CH:3]([CH2:17][CH2:18][O:19][S:20]([C:23]4[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH2:4][CH2:5][C:6]=3[O:10][N:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 19786582HCID 19786582, compound

Product 1

HCID 19786608HCID 19786608, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

In 30 ml pyridine was dissolved 4-hydroxy-5-(2-hydroxyethyl)-3-phenyl-4,5,6,7-tetrahydro-1,2-benzisoxazole (2.1 g) and the mixture was cooled to 0° C. Tosyl chloride (1.54 g) was added and the solution was stirred at 0° C. for 30 minutes. The reaction mixture was poured into ice water, then extracted four times with ether. The mixture was dried (Na2SO4) and then concentrated at room temperature to yield 2.67 g of 3-phenyl-5-(2-tosyloxyethyl)-4-hydroxy-4,5,6,7-tetrahydro-1,2-benzisoxazole.

Workup

  1. extractionextracted four times with ether
  2. dry with materialThe mixture was dried (Na2SO4)
  3. concentrationconcentrated at room temperature

Sources & evidence

ORD record
ord-f59d8666049245328147ae19b3151179
Source dataset
uspto-grants-1993_10
Patent number
US05256672

Reaction notes

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