Triethylamine → HCID 13272679, compound

HRID 1956752Notes

Reaction equation

HRID 1956752 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:6][CH2:5][C@H:4]1[CH2:7][OH:8].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)(Cl)Cl>[CH3:16][S:17]([O:1][CH2:2][C@@H:3]1[CH2:6][CH2:5][C@H:4]1[CH2:7][O:8][S:17]([CH3:16])(=[O:19])=[O:18])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12602732trans-cyclobutane-1,2-diyldimethanol

Product 1

HCID 13272679HCID 13272679, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the compound (18) (8.50 g; 0.0733 mol) and triethylamine (22.20 g; 0.22 mol) in chloroform (100 ml), methanesulfonyl chloride (16.79 g; 0.147 mol) is dropwise added under ice-cooling, and the resultant mixture is stirred for 7 hours at room temperature. The reaction mixture is washed with water, dried and concentrated under reduced pressure to give trans-1,2-bis(methanesulfonyloxymethyl)cyclobutane (19) (18.50 g). m.p., 60° to 62° C. (crystallized from ether).

Workup

  1. temperaturecooling
  2. washThe reaction mixture is washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-645fe39b3bae4ecdab90708070bc212e
Source dataset
uspto-grants-1998_07
Patent number
US05780632

Reaction notes

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