Triethylamine → 3-(4-(hydroxymethyl)phenylthio)dihydrofuran-2(3H)-one

HRID 1987828Notes

Reaction equation

HRID 1987828 reaction equation
Br[CH:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7].[SH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)Cl>[OH:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([S:8][CH:2]2[CH2:6][CH2:5][O:4][C:3]2=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 4677905(4-Sulfanylphenyl)methanol

Product 1

HCID 690718993-(4-(hydroxymethyl)phenylthio)dihydrofuran-2(3H)-oneYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-bromo-dihydrofuran-2(3H)-one (2.35 g, 14.3 mmol) was added to a solution of (4-mercaptophenyl)methanol (2.00 g, 14.0 mmol) and triethylamine (2.4 mmol, 17 mmol). The reaction was stirred at room temperature overnight, then was diluted with CH2Cl2 and washed sequentially with saturated NH4Cl and NaCl solutions. The organics were dried over MgSO4 and concentrated under reduced pressure to provide the product as a viscous oil (2.3 g, 72%).

Workup

  1. washwashed sequentially with saturated NH4Cl and NaCl solutions
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-be28c555b33947a68fa454b43186ba49
Source dataset
uspto-grants-2009_06
Patent number
US07553842B2

Reaction notes

Loading…