4-Toluenesulfonyl chloride → (+)-3-[2-(Benzyloxy)-4-methoxyphenyl]-2-hydroxypropyl 4-methylbenzenesulfonate

HRID 2115903Notes

Reaction equation

HRID 2115903 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[CH2:17][CH:18]([OH:21])[CH2:19][OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>N1C=CC=CC=1>[CH3:32][C:22]1[CH:27]=[CH:26][C:25]([S:28]([O:20][CH2:19][CH:18]([OH:21])[CH2:17][C:10]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68966303(+/-)-3-[2-(Benzyloxy)-4-methoxyphenyl]propane-1,2-diol

Product 1

HCID 86599058(+)-3-[2-(Benzyloxy)-4-methoxyphenyl]-2-hydroxypropyl 4-methylbenzenesulfonateYield 91.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (±)-3-[2-(benzyloxy)-4-methoxyphenyl]propane-1,2-diol (30.50 g, 0.106 mol) in anhydrous pyridine (600 mL) cooled to 0° C. under a nitrogen atmosphere was added p-toluenesulfonyl chloride (22.18 g, 0.116 mol). The reaction mixture was allowed to stir at 0° C. for 12 h. The reaction mixture was quenched by the addition of water (10 mL). The reaction mixture was diluted with ethyl acetate (750 mL) and the organic layer was washed with aqueous hydrogen chloride (6 N, 4×400 mL), saturated aqueous sodium chloride (300 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 2:8) gave 42.84 g (91%) of (±)-3-[2-(benzyloxy)-4-methoxyphenyl]-2-hydroxypropyl 4-methylbenzenesulfonate as a colorless oil. Rf=0.28 (silica, ethyl acetate:hexanes 2:8); Anal. calcd. for C24H26O6S: C, 65.14; H, 5.92. Found: C, 64.59; H, 5.72.

Workup

  1. customThe reaction mixture was quenched by the addition of water (10 mL)
  2. additionThe reaction mixture was diluted with ethyl acetate (750 mL)
  3. washthe organic layer was washed with aqueous hydrogen chloride (6 N, 4×400 mL), saturated aqueous sodium chloride (300 mL)
  4. dry with materialdried (magnesium sulfate)
  5. customthe solvent was removed in vacuo
  6. customto give a crude oil
  7. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 2:8)

Sources & evidence

ORD record
ord-f11d77571c654b85bf9a8b969e909153
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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