Triethylamine → 1,2-Bis(methanesulfonyloxymethyl)cyclohexane, (1R,2R)-

HRID 1734226Notes

Reaction equation

HRID 1734226 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[CH2:9][OH:10].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(#N)C>[CH3:18][S:19]([O:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[CH2:9][O:10][S:19]([CH3:18])(=[O:21])=[O:20])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11217323rel-(1R,2R)-1,2-Cyclohexanedimethanol

Product 1

HCID 2534831,2-Bis(methanesulfonyloxymethyl)cyclohexane, (1R,2R)-Yield 50.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The thus obtained compound (2) (5.1 g; 35.4 mmol) is dissolved in triethylamine (10.37 g; 103 mmol) and acetonitrile (127 ml), and methanesulfonyl chloride (8.13 g; 71 mmol) is dropwise added thereto under ice-cooling. The resultant mixture is ice-cooled for 1 hour and allowed to react at room temperature for 3 hours. The reaction mixture is washed with water, dried and concentrated, followed by addition of diethyl ether. Precipitated crystals are collected by filtration to give trans-1,2-bis(methanesulfonyloxymethyl)cyclohexane (3) (5.4 g).

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooled for 1 hour
  3. customto react at room temperature for 3 hours
  4. washThe reaction mixture is washed with water
  5. customdried
  6. concentrationconcentrated
  7. additionfollowed by addition of diethyl ether
  8. customPrecipitated crystals
  9. filtrationare collected by filtration

Sources & evidence

ORD record
ord-99dcb244539e4163b87300df8eff2571
Source dataset
uspto-grants-1996_07
Patent number
US05532372

Reaction notes

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