Water → phenylacetic anhydride

HRID 595783Notes

Reaction equation

HRID 595783 reaction equation
[OH-:1].[Na+].N[C@@:4]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([C:6]#C)C.CC[O:16][C:17]([CH3:19])=[O:18].O>C(Cl)(Cl)Cl>[C:8]1([CH2:19][C:17]([O:16][C:6](=[O:1])[CH2:4][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:18])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 16090548HCID 16090548, compound

Product 1

HCID 316205phenylacetic anhydride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 1.50 M sodium hydroxide solution was added to the hydrochloride salt of (S)-2-amino-2-cyclohexyl-3-butyne 30 (1 equiv). A solution of anhydride (0.17 M, 1 equiv) in chloroform was added to the above solution and heated at reflux for 24 h. The reaction mixture was transferred to a reparatory funnel, and EtOAc (150 mL) and water (15 mL) were added. The organic layer was washed with brine (25 mL), 10 M aqueous sodium hydroxide solution (25 mL×4), brine (25 mL×4), and water (25 mL×2). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography (1:1 hexanes:EtOAc) to afford the desired product.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. customThe reaction mixture was transferred to a reparatory funnel
  4. washThe organic layer was washed with brine (25 mL), 10 M aqueous sodium hydroxide solution (25 mL×4), brine (25 mL×4), and water (25 mL×2)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe product was purified by flash chromatography (1:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-2ac87404f6dc4d5399d9dc53b663471a
Source dataset
uspto-grants-2016_01
Patent number
US09245290B2

Reaction notes

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