Dichloromethane → HCID 9923209, compound

HRID 478997Notes

Reaction equation

HRID 478997 reaction equation
[CH2:1]([Cl:3])Cl.Cl[C:5]1[CH:6]=[C:7]([C@@H:11]([O:14][C:15]([O:18][CH3:19])([CH3:17])[CH3:16])[CH2:12][OH:13])[CH:8]=[CH:9]C=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(N(CC)CC)C>[CH3:20][S:21]([O:13][CH2:12][C@@H:11]([C:7]1[CH:8]=[CH:9][C:1]([Cl:3])=[CH:5][CH:6]=1)[O:14][C:15]([O:18][CH3:19])([CH3:17])[CH3:16])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 69333899HCID 69333899, compound

Product 1

HCID 9923209HCID 9923209, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into methylene chloride (20 ml) were added (R)-2-(3-chlorophenyl)-2-(1-methoxy-1-methylethyloxy)ethanol obtained in 3) above (5.0 g) and triethylamine (3.9 g) and further, under ice-cooling and dropwise, methanesulfonyl chloride (2.46 g), and the resulting mixture was stirred at the same temperature for 1 hour. The reaction mixture was washed with water, and the organic layer was washed with a saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. The desiccant was filtered off and the solvent was distilled off to obtain a colorless oily compound mentioned above (6.33 g, 96.0%). The optical purity of the product obtained was 99.9% e.e.

Workup

  1. temperaturefurther, under ice-cooling
  2. washThe reaction mixture was washed with water
  3. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered off
  6. distillationthe solvent was distilled off
  7. customto obtain a colorless oily compound
  8. customThe optical purity of the product obtained

Sources & evidence

ORD record
ord-2f2bac4cf69a4374a931a0ab9703a777
Source dataset
uspto-grants-2003_11
Patent number
US06642395B1

Reaction notes

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