Acetic Acid → HCID 23094148, compound

HRID 2172546Notes

Reaction equation

HRID 2172546 reaction equation
P(=O)(O)(O)O.[Cl:6][C:7]1[S:11][C:10]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:9][CH:8]=1.C(O)(=O)C>O>[Cl:6][C:7]1[S:11][C:10]2[CH2:12][CH2:13][CH2:14][C:15](=[O:17])[C:9]=2[CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1004Phosphoric AcidHCID 28895829HCID 28895829, compound

Product 1

HCID 23094148HCID 23094148, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

First 0.096 ml (1.41 mmol) of orthophosphoric acid and then 4.12 g (20.14 mmol) of 4-(5-chloro-2-thienyl)butanoic acid are added to 5 ml of acetic acid, and the mixture is stirred at 120° C. for 2.5 h. The cooled reaction mixture is added to water and extracted with dichloromethane, and the extract is washed with 2 M NaOH. After washing with water, the organic phase is dried over sodium sulphate and concentrated under reduced pressure. The residue is extracted with diethyl ether. Undissolved crystals are filtered off with suction and discarded. The ether phase is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate). This gives 1.07 g of 2-chloro-6,7-dihydro-1-benzothiophen-4(5H)-one.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with dichloromethane
  3. washthe extract is washed with 2 M NaOH
  4. washAfter washing with water
  5. dry with materialthe organic phase is dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. extractionThe residue is extracted with diethyl ether
  8. filtrationUndissolved crystals are filtered off with suction
  9. concentrationThe ether phase is concentrated under reduced pressure
  10. customthe residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-dfcf8a7c7de34190b6e57d78cfb25f9b
Source dataset
uspto-grants-2015_06
Patent number
US09055743B2

Reaction notes

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