HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 2221304
Notes
Print preview

Reaction equation

HRID 2221304 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59710879(7-benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(R)-yl)-methanol

Product 1

HCID 59710884methansulfonic acid 7-benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(S)-yl-methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes