4-Toluenesulfonyl chloride → [7-(methylsulfonyl)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate

HRID 39033Notes

Reaction equation

HRID 39033 reaction equation
[CH3:1][S:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH:11]([CH2:15][OH:16])[O:12]2)=[CH:7][CH:6]=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:16][CH2:15][CH:11]2[CH2:10][CH2:9][C:8]3[C:13](=[CH:14][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[O:12]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 66878595[7-(Methylsulfonyl)-3,4-dihydro-2H-chromen-2-YL]methanol

Product 1

HCID 86652940[7-(methylsulfonyl)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Preparation according to Preparation 22 using [7-(methylsulfonyl)-3,4-dihydro-2H-chromen-2-yl]methanol (0.4 g, 1.65 mmol), DCM (25 ml), p-toluenesulfonyl chloride (0.47 g, 2.5 mmol), TEA (0.28 ml, 2.0 mmol) and 4-DMAP (0.24 g, 2.0 mmol) stirred for overnight at room temperature. Yield: 0.59 g. MS m/z (rel. intensity, 70 eV) 419 (62), 416 (14), 415 (25), 414 (bp), 397 (M+1, 39).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-a9d10e1dd32d487683c33f27664c804e
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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