4-Toluenesulfonyl chloride → [7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

HRID 38986Notes

Reaction equation

HRID 38986 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][CH:11]([CH2:14][OH:15])[O:10][C:9]=2[CH:16]=1)(=[O:4])=[O:3].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:15][CH2:14][CH:11]2[O:10][C:9]3[CH:16]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=[CH:7][C:8]=3[O:13][CH2:12]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 66878354[7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol

Product 1

HCID 86652933[7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonateYield 74.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of [7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (0.9 g, 3.7 mmol), p-toluenesulfonyl chloride (1.0 g, 5.5 mmol), TEA (0.76 ml, 5.5 mmol) and 4-DMAP (0.4 g, 3.7 mmol) in DCM (20 ml) was stirred at room temperature for 1 h and 30 min. The solution was diluted with DCM and washed with HCl (1 N), water and brine. The organic phase was dried and concentrated to give the title compound (1.1 g). MS m/z (rel. intensity, 70 eV) 398 (M+, 51), 226 (bp), 225 (23), 213 (30), 91 (62).

Workup

  1. washwashed with HCl (1 N), water and brine
  2. customThe organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4a3973541d074a80a678ea37fc7e3360
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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