4-Toluenesulfonyl chloride → (+/-)-3-[1-(Benzyloxy)-4-chloro-2-naphthyl]-2-hydroxypropyl 4-methylbenzenesulfonate

HRID 13940Notes

Reaction equation

HRID 13940 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([Cl:19])=[CH:11][C:10]=1[CH2:20][CH:21]([OH:24])[CH2:22][OH:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>N1C=CC=CC=1>[CH3:35][C:25]1[CH:30]=[CH:29][C:28]([S:31]([O:23][CH2:22][CH:21]([OH:24])[CH2:20][C:10]2[CH:11]=[C:12]([Cl:19])[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68583747(+/-)-3-[1-(Benzyloxy)-4-chloro-2-naphthyl]propane-1,2-diol

Product 1

HCID 86598554(+/-)-3-[1-(Benzyloxy)-4-chloro-2-naphthyl]-2-hydroxypropyl 4-methylbenzenesulfonateYield 80.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Treatment of (±)-3-[1-(benzyloxy)-4-chloro-2-naphthyl]propane-1,2-diol (24 g, 0.07 mol) with p-toluenesulfonyl chloride (14 g, 0.074 mol) in pyridine (600 mL) generally according to the procedure described for Intermediate 18 gave 27.9 g (80%) of (±)-3-[1-(benzyloxy)-4-chloro-2-naphthyl]-2-hydroxypropyl 4-methylbenzenesulfonate as a white solid. mp 85-87° C.; Anal. calcd. for C27H25ClO5S: C, 65.25; H, 5.07. Found: C, 65.37; H, 4.97.

Sources & evidence

ORD record
ord-8ed7009cdc7540738319bf85219fd384
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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