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

HRID 339088Notes

Reaction equation

HRID 339088 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 27335882-Methoxy-1-propanol, (2R)-

Product 1

HCID 13896527(2R)-2-methoxypropyl 4-methylbenzene-1-sulfonateYield 55.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of crude (R)-2-methoxypropan-1-ol (4.30 g, 47.7 mmol) in DCM (200 mL) was added Et3N (10.0 mL, 71.6 mmol). A solution of toluene sulfonyl chloride (10.9 g, 57.3 mmol) in DCM (80 mL) was added dropwise at 0° C. under nitrogen. The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction was diluted with DCM, washed with saturated aqueous NaHCO3 solution and brine, dried and concentrated. The residue was purified by flash chromatography on silica gel (hexanes:EtOAc, 10:1 to 4:1) to give (R)-2-methoxypropyl 4-methylbenzenesulfonate (6.43 g, 55% for three steps).

Workup

  1. washwashed with saturated aqueous NaHCO3 solution 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-8da25985801e481ab8f216b901773cd4
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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