Ethanethiol → HCID 22228637, compound

HRID 1744287Notes

Reaction equation

HRID 1744287 reaction equation
C[O:2][C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[C:22]([CH3:23])=[CH:21][C:11]3[C:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][O:14][C:10]=3[C:9]=2[CH3:24])=[CH:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(S)C>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[C:22]([CH3:23])=[CH:21][C:11]3[C:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][O:14][C:10]=3[C:9]=2[CH3:24])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 22228617HCID 22228617, compound

Product 1

HCID 22228637HCID 22228637, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.74 g (2.09 mmol) of ethyl 2-[6-(4-methoxyphenoxy)-5,7-dimethyl-1-benzofuran-3-yl]acetate, dissolved in 1 ml of dichloromethane, is [lacuna], at 0° C., to a solution of 0.84 g (6.26 mmol) of aluminum chloride and 0.65 g (10.44 mmol) of ethanethiol in 10 ml of dichloromethane. The reaction mixture is stirred overnight at room temperature, after which the solvent is removed in vacuo and the residue is subjected to chromatographic purification (cyclohexane/ethyl acetate=5.1). 0.52 g (73%) of ethyl 2-[6-(4-hydroxyphenoxy)-5,7-dimethyl-1-benzofuran-3-yl]acetate is obtained.

Workup

  1. customat 0° C.
  2. customafter which the solvent is removed in vacuo
  3. customthe residue is subjected to chromatographic purification (cyclohexane/ethyl acetate=5.1)

Sources & evidence

ORD record
ord-2f8518fcef274a79a9bf48c961969ec4
Source dataset
uspto-grants-2006_03
Patent number
US07015246B2

Reaction notes

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