4-Toluenesulfonyl chloride → (+/-)-[7-(4-Chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate

HRID 2116061Notes

Reaction equation

HRID 2116061 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[O:15][CH:14]([CH2:17][OH:18])[CH2:13][C:12]=3[CH:11]=[CH:10][CH:9]=2)=[C:4]([CH3:19])[CH:3]=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>>[CH3:30][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:18][CH2:17][CH:14]2[CH2:13][C:12]3[CH:11]=[CH:10][CH:9]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=4[CH3:19])[C:16]=3[O:15]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68964315(+/-)-[7-(4-Chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanol

Product 1

HCID 86599146(+/-)-[7-(4-Chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonateYield 93.2%

Procedure

Treatment of (±)-[7-(4-chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanol (2.78 g, 10.11 mmol) with p-toluenesulfonyl chloride (2.31 g, 12.14 mol) generally according to the procedure described for Intermediate 10 gave 4.04 g (93%) of (±)-[7-(4-chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate as a yellow oil. Anal. calcd. for C23H21ClO4S: C, 64.4; H, 4.93. Found: C, 64.24; H, 4.93.

Sources & evidence

ORD record
ord-1e25ec4cd0a14e50a20002ef34616b82
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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