Hydrochloric Acid → HCID 54539291, compound

HRID 1584882Notes

Reaction equation

HRID 1584882 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[C:18]2[O:19][C@@H:20]([CH2:23][OH:24])[CH2:21][O:22][C:17]=2[CH:16]=[CH:15][CH:14]=1.Cl>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:24][CH2:23][C@@H:20]2[O:19][C:18]3[C:13]([Cl:12])=[CH:14][CH:15]=[CH:16][C:17]=3[O:22][CH2:21]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 54521797HCID 54521797, compound

Product 1

HCID 54539291HCID 54539291, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 4-toluenesulphonyl chloride (3.15 g) in dry pyridine (15 ml) was added to a solution of (S)-8-chloro-1,4-benzodioxan-2-ylmethanol (3.32 g; prepared in a similar manner to that described above) in dry pyridine (40 ml) and the mixture stirred at ambient temperature for 18 hours, then poured onto ice and dilute hydrochloric acid added to give pH4. The mixture was extracted with dichloromethane (2×200 ml) and the combined extracts washed with brine and dried over magnesium sulphate. The solvent was evaporated to give (R)-8-chloro-1,4-benzodioxan-2-ylmethyl 4-toluenesulphonate (5.21 g) as a pale yellow solid.

Workup

  1. customprepared in a similar manner to that
  2. additionadded
  3. customto give pH4
  4. extractionThe mixture was extracted with dichloromethane (2×200 ml)
  5. washthe combined extracts washed with brine
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-dfb507a9156346d795420fc124a650f6
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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