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

HRID 1907256Notes

Reaction equation

HRID 1907256 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.C(N(CC)CC)C.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:10][CH2:9][CH2:8][C@H:7]([OH:11])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 6950537(1S)-1-phenylpropane-1,3-diol

Product 1

HCID 11449624(S)-3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonateYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-1-phenylpropane-1,3-diol (500 mg, 3.28 mmol) and triethylamine (399 mg, 3.94 mmol) in CH2Cl2 (5 mL) was added 4-methylbenzene-1-sulfonyl chloride (626 mg, 3.28 mol) slowly at 0° C., and the reaction mixture was stirred at rt for 2 h. The reaction solution was dried over Na2SO4 and concentrated to give the crude product, which was purified by preparative TLC (3:1 Petroleum ether/EtOAc) to give (S)-3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate (576 mg, 57%). 1H NMR (400 MHz, CDCl3): δ=1.91-2.00 (m, 3H), 2.48 (s, 2H), 4.00 (m; 1H), 4.22 (m, 1H), 4.75 (m, 2H), 7.25-7.30 (m, 7H), 7.75 (d, 2H).

Workup

  1. dry with materialThe reaction solution was dried over Na2SO4
  2. concentrationconcentrated
  3. customto give the crude product, which
  4. customwas purified by preparative TLC (3:1 Petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-83615ce36ae8442f8fda391c01dc7aa6
Source dataset
uspto-grants-2013_12
Patent number
US08598160B2

Reaction notes

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