Triethylamine → 3-Mesyloxypropyl 2-methoxy-3-(12-cyclohexyldodecyloxy)propyl sulfone

HRID 231272Notes

Reaction equation

HRID 231272 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5]([CH2:8][CH:9]([O:30][CH3:31])[CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)(=[O:7])=[O:6].C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>ClCCl>[CH3:31][O:30][CH:9]([CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1)[CH2:8][S:5]([CH2:4][CH2:3][CH2:2][O:1][S:40]([CH3:39])(=[O:42])=[O:41])(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 536553312-Methoxy-3-(12-cyclohexyldodecyloxy)propyl 3-hydroxypropyl sulfone

Product 1

HCID 200348483-Mesyloxypropyl 2-methoxy-3-(12-cyclohexyldodecyloxy)propyl sulfoneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 100 ml of dichloromethane are dissolved 8.9 g of 2-methoxy-3-(12-cyclohexyldodecyloxy)propyl 3-hydroxypropyl sulfone and 3.7 ml of triethylamine, to which 3.0 g of methanesulfonyl chloride is added dropwise with stirring under ice cooling. After 2 hours stirring at room temperature, the reaction solution is washed with water, an aqueous sodium bicarbonate solution and water, and dried. The solvent is then distilled off under reduced pressure to leave 10.4 g of the captioned compound.

Workup

  1. stirringAfter 2 hours stirring at room temperature
  2. washthe reaction solution is washed with water
  3. dry with materialan aqueous sodium bicarbonate solution and water, and dried
  4. distillationThe solvent is then distilled off under reduced pressure

Sources & evidence

ORD record
ord-7b72b371a23642eb80240b8937b93466
Source dataset
uspto-grants-1989_07
Patent number
US04845219

Reaction notes

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