4-Toluenesulfonyl chloride → (S)-3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate

HRID 1509859Notes

Reaction equation

HRID 1509859 reaction equation
[C:1]1([C@@H:7]([OH:11])[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1N2CCN(CC2)C1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[OH:11][C@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][CH2:9][O:10][S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 9237DabcoHCID 6950537(1S)-1-phenylpropane-1,3-diol

Product 1

HCID 11449624(S)-3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-1-phenyl-propane-1,3-diol (0.5 g, 3.3 mmol) and triethylenediamine (368 mg, 3.3 mmol) in DCM (40 mL) cooled to 0° C. was added dropwise p-toluenesulfonyl chloride (1.96 g, 0.0103 mol) in DCM (20 mL). The reaction mixture was stirred for 1 h and then filtered through a pad of silica. The silica was washed with DCM and the filtrate was concentrated to give the title compound as a crude oil (0.485 mg).

Workup

  1. filtrationfiltered through a pad of silica
  2. washThe silica was washed with DCM
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d621e9cf02f44965b48e385753edcb47
Source dataset
uspto-grants-2012_07
Patent number
US08211894B2

Reaction notes

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