4-Toluenesulfonyl chloride → (+/-)-3-[4-(benzyloxy)-6-chloro-2,3-dihydro-1H-inden-5-yl]-2-hydroxypropyl 4-methylbenzenesulfonate

HRID 13947Notes

Reaction equation

HRID 13947 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([CH2:18][CH:19]([OH:22])[CH2:20][OH:21])=[C:16]([Cl:23])[CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][CH2:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>N1C=CC=CC=1>[CH3:34][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O:21][CH2:20][CH:19]([OH:22])[CH2:18][C:17]2[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:10]3[C:14](=[CH:15][C:16]=2[Cl:23])[CH2:13][CH2:12][CH2:11]3)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68584309(+/-)-3-[4-(benzyloxy)-6-chloro-2,3-dihydro-1H-inden-5-yl]propane-1,2-diol

Product 1

HCID 86598558(+/-)-3-[4-(benzyloxy)-6-chloro-2,3-dihydro-1H-inden-5-yl]-2-hydroxypropyl 4-methylbenzenesulfonateYield 77%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Treatment of (±)-3-[4-(benzyloxy)-6-chloro-2,3-dihydro-1H-inden-5-yl]propane-1,2-diol (5.60 g, 0.0168 mol) with p-toluenesulfonyl chloride (3.70 g, 0.0194 mol) in pyridine (200 mL) generally according to the procedure described for Intermediate 18 provided 6.30 g (77%) of (±)-3-[4-(benzyloxy)-6-chloro-2,3-dihydro-1H-inden-5-yl]-2-hydroxypropyl 4-methylbenzenesulfonate as a light yellow oil. 1H NMR (DMSO-d6) 8H 7.65(d, 2H); 7.40(m, 7H); 7.05(s, 1H); 5.25(s, 1H); 4.90(s, 2H); 3.80(m, 3H); 2.90(m, 2H); 2.80(m, 3H); 2.65(dd, 1H); 2.40(s, 3H); 2.00(m, 2H).

Sources & evidence

ORD record
ord-afa0de4fa1314bc2ab626f5a63fc339d
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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