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Hydrochloric Acid → Methanesulfonic acid 2-(2,3-dihydrobenzofuran-4-yl)-ethyl ester

HRID 1602405
Notes
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Reaction equation

HRID 1602405 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][CH2:11][OH:12])[C:4]=2[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].Cl>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][CH2:11][O:12][S:21]([CH3:20])(=[O:23])=[O:22])[C:4]=2[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 196116722-(2,3-Dihydro-1-benzofuran-4-yl)ethan-1-ol

Product 1

HCID 54501623Methanesulfonic acid 2-(2,3-dihydrobenzofuran-4-yl)-ethyl ester

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A solution of 2-(2,3-dihydrobenzofuran-4-yl)-ethanol (1.13 g) in dichloromethane (11 ml) was treated with triethylamine (1.25 ml), followed by methanesulfonyl chloride (0.64 ml). After 5 min the reaction mixture was poured into 2M hydrochloric acid (10 ml) and extracted with dichloromethane (2×10 ml). The combined extracts were washed with water (10 ml), dried (Na2SO4) and the solvent evaporated to give the title compound (1.76 g) as a yellow oil.

Workup

  1. extractionextracted with dichloromethane (2×10 ml)
  2. washThe combined extracts were washed with water (10 ml)
  3. dry with materialdried (Na2SO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-564546274a1a4379ae83c396ab8078cc
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05981572

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes