Triethylamine → methansulfonic acid 7-benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(S)-yl-methyl ester

HRID 2221304Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1([S:12]([C:15]2[CH:16]=[CH:17][C:18]3[O:23][CH2:22][C@@H:21]([CH2:24][OH:25])[O:20][C:19]=3[CH:26]=2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>ClCCl>[C:6]1([S:12]([C:15]2[CH:16]=[CH:17][C:18]3[O:23][CH2:22][C@@H:21]([CH2:24][O:25][S:2]([CH3:1])(=[O:4])=[O:3])[O:20][C:19]=3[CH:26]=2)(=[O:14])=[O:13])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methanesulfonyl chloride (0.550 g; 0.0048 mol) at 0° C. was added drop-wise to a solution of (7-benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(R)-yl)-methanol (0.73 g; 0.00238 mol) and triethyl amine (0.48 g; 0.0048 mol) in dichloromethane (10 mL). The mixture was stirred at 0° C. for 45 minutes, and then diluted with dichloromethane (20 mL), washed with water, dried (Na2SO4) and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel (hexane-ethyl acetate; 1:1) to give methansulfonic acid 7-benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(S)-yl-methyl ester as a foam (0.67 g; 73%): MS (M+H)+ 385.

Workup

washwashed with water
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe crude material was purified by flash chromatography on silica gel (hexane-ethyl acetate; 1:1)

Sources & evidence

ORD record: ord-ef7c402d563941b9b5cdbf241bce158f
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368567B2

Reaction notes

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