Triethylamine → (2S)-2-methoxypropyl 4-methylbenzene-1-sulfonate

HRID 339085Notes

Reaction equation

HRID 339085 reaction equation
[CH3:1][O:2][C@@H:3]([CH3:6])[CH2:4][OH:5].[CH3:7]CN(CC)CC.[C:14]1(C)[C:15]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1>C(Cl)Cl>[CH3:7][C:18]1[CH:19]=[CH:14][C:15]([S:20]([O:5][CH2:4][C@@H:3]([O:2][CH3:1])[CH3:6])(=[O:21])=[O:22])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 6424022-Methoxy-1-propanol, (2S)-

Product 1

HCID 13896528(2S)-2-methoxypropyl 4-methylbenzene-1-sulfonateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of (S)-2-methoxypropan-1-ol (1.00 g, 11.1 mmol) in DCM (50 mL) was added Et3N (2.33 mL, 16.6 mmol). A solution of toluene sulfonyl chloride (2.54 g, 13.3 mmol) in DCM (20 mL) was added dropwise at 0° C. under nitrogen. The reaction mixture was allowed to warm to ambient temperature and was stirred overnight. The reaction was diluted with DCM, washed with saturated aqueous NaHCO3 and brine, dried and concentrated. The residue was purified by flash chromatography on silica gel (hexanes:EtOAc, 10:1 to 4:1) to give (S)-2-methoxypropyl 4-methylbenzenesulfonate (2.03 g, 75%).

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel (hexanes:EtOAc, 10:1 to 4:1)

Sources & evidence

ORD record
ord-3296c8bcd47a48269f7dd2b662c9a625
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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