Methyl Thioglycolate → Methyl ((4-(4-chlorophenyl)-1-(4-hydroxyphenyl)-1-butyl)thio)acetate

HRID 2253752Notes

Reaction equation

HRID 2253752 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)O)=[CH:4][CH:3]=1.[C:20]([O:24][CH3:25])(=[O:23])[CH2:21][SH:22]>C(Cl)Cl.[Zn+2].[I-].[I-]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]([S:22][CH2:21][C:20]([O:24][CH3:25])=[O:23])[C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 16907Methyl ThioglycolateHCID 197458724-(4-(4-Chlorophenyl)-1-hydroxybutyl)phenol

Product 1

HCID 54384776Methyl ((4-(4-chlorophenyl)-1-(4-hydroxyphenyl)-1-butyl)thio)acetate

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of the alcohol (0.23 g) (Step VI) in CH2Cl2 (5 mL) and methyl thioglycolate (80 μL) was added ZnI2 (10 mg). The mixture was stirred 2 hrs, buffer (pH 7) was added. The mixture was extracted with ethyl acetate, which was dried and evaporated. Flash chromatography using 5% ethyl acetate in toluene afforded the title compound.

Workup

  1. additionbuffer (pH 7) was added
  2. extractionThe mixture was extracted with ethyl acetate, which
  3. customwas dried
  4. customevaporated

Sources & evidence

ORD record
ord-d8633e2412724c49b74225f7a8783f4f
Source dataset
uspto-grants-1993_08
Patent number
US05232916

Reaction notes

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