Ethanol → HCID 118268374, compound

HRID 1663014Notes

Reaction equation

HRID 1663014 reaction equation
[CH:1]1([S:4][C:5]2[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.S(Cl)(Cl)=O.[CH2:19](O)[CH3:20]>>[CH2:19]([O:13][C:12](=[O:14])[CH2:11][C:8]1[CH:9]=[CH:10][C:5]([S:4][CH:1]2[CH2:2][CH2:3]2)=[CH:6][CH:7]=1)[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 59347115[4-(Cyclopropylsulfanyl)phenyl]acetic acid

Product 1

HCID 118268374HCID 118268374, compound

Procedure

[4-(Cyclopropylthio)phenyl]acetic acid (13.1 g) was dissolved into ethanol (52 mL). Then, thionyl chloride (5.51 mL) was added dropwise while cooling by an ice bath, and the resulting mixture was stirred for 90 minutes at room temperature. This reaction mixture was concentrated under reduced pressure, and the resulting residue was dissolved in ethyl acetate (125 mL). This ethyl acetate solution was washed with water (4×25 mL) and then a saturated aqueous sodium carbonate solution (25 mL). The resulting mixture was dried over anhydrous sodium sulfate, then filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant; hexane:ethyl acetate=3:1) to obtain ethyl[4-(cyclopropylthio)phenyl]acetate (15.5 g).

Workup

  1. temperaturewhile cooling by an ice bath
  2. concentrationThis reaction mixture was concentrated under reduced pressure
  3. dissolutionthe resulting residue was dissolved in ethyl acetate (125 mL)
  4. washThis ethyl acetate solution was washed with water (4×25 mL)
  5. dry with materialThe resulting mixture was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluant; hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-6966b730f59a402eae078b5e54155911
Source dataset
uspto-grants-2011_10
Patent number
US08034819B2

Reaction notes

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