Water → 2-[(2-Hydroxyethyl)thio]ethyl benzoate

HRID 1786991Notes

Reaction equation

HRID 1786991 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].[C:5]([O:13][CH2:14][CH2:15]I)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(C(C)C)C(C)C)C.O>CN(C)C=O>[C:5]([O:13][CH2:14][CH2:15][S:1][CH2:2][CH2:3][OH:4])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15672-MercaptoethanolHCID 81531DiisopropylethylamineHCID 125101182-Iodoethyl Benzoate

Product 1

HCID 544395062-[(2-Hydroxyethyl)thio]ethyl benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-mercaptoethanol (1.52 mL), 2-iodoethyl benzoate (6.00 g) and ethyldiisopropylamine (4.53 mL) in N,N-dimethylformamide (60 mL) was stirred at 40° C. for 3 days. Water was added to the reaction system and the mixture was extracted with ethyl acetate. The organic layer washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=4:1→3:7) to give the title compound (3.77 g) as an orange oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=4:1→3:7)

Sources & evidence

ORD record
ord-77393fc65ff34169adaaff01e832835b
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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