Water → HCID 10570152, compound

HRID 1584869Notes

Reaction equation

HRID 1584869 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[O:21][CH2:20][C@H:19]([CH2:22][OH:23])[O:18][C:17]=2[CH:24]=1.O>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:23][CH2:22][C@@H:19]2[O:18][C:17]3[CH:24]=[C:13]([Cl:12])[CH:14]=[CH:15][C:16]=3[O:21][CH2:20]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chloride3×HCID 54343476HCID 54343476, compound

Product 1

HCID 10570152HCID 10570152, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Toluenesulphonyl chloride (5.9 g) was added to a solution of (S)-7-chloro-1,4-benzodioxan-2-ylmethanol (6.0 g; prepared by the method described above) in pyridine (40 ml) and the mixture stirred for 4 hours. More 4-toluenesulphonyl chloride (250 mg) was added, stirring continued for 2 hours, then further 4-toluenesulphonyl chloride (250 mg) was added and stirring continued for 1 hour. The mixture was poured into water (200 ml) and extracted with ethyl acetate (2×200 ml). The combined extracts were washed with hydrochloric acid (2M; 2×200 ml), saturated aqueous sodium bicarbonate solution (2×200 ml) and brine (200 ml), then dried over magnesium sulphate. The solvent was removed in vacuo and the residue recrystallised from ether to give (R)-7-chloro-1,4-benzodioxan-2-ylmethyl 4-toluenesulphonate (7.00 g) m.p. 90-91° C.

Workup

  1. customprepared by the method
  2. stirringstirring
  3. waitcontinued for 2 hours
  4. stirringstirring
  5. waitcontinued for 1 hour
  6. extractionextracted with ethyl acetate (2×200 ml)
  7. washThe combined extracts were washed with hydrochloric acid (2M; 2×200 ml), saturated aqueous sodium bicarbonate solution (2×200 ml) and brine (200 ml)
  8. dry with materialdried over magnesium sulphate
  9. customThe solvent was removed in vacuo
  10. customthe residue recrystallised from ether

Sources & evidence

ORD record
ord-f88e4cecf6834ba6af3bae6456bd6949
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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