Acetic Anhydride → HCID 178471963, compound

HRID 1396119Notes

Reaction equation

HRID 1396119 reaction equation
[O:1]=[C:2]([C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([F:17])[C:10]=1[F:18])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C([O:26][CH2:27][CH3:28])(OCC)OCC.[NH2:29][CH:30](C1CC1)O.[C:35](OC(=O)C)(=O)[CH3:36]>>[OH:26][CH2:27][C:28]1([NH:29][CH:30]=[C:3]([C:2](=[O:1])[C:9]2[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([F:17])[C:10]=2[F:18])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:36][CH2:35]1

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoateHCID 45489680HCID 45489680, compound

Product 1

HCID 178471963HCID 178471963, compound

Procedure

A stirred solution of ethyl 3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate (10.0 g, 37.8 mmol), acetic anhydride (50 mL) and triethyl orthoformate (10.0 mL, 56.7 mmol) was heated at 130° C. for 3 h. The mixture was concentrated and dried under high vacuum for 5 hours. The crude product was dissolved in DCM (50 mL) and then 1-amino-1-cyclopropylmethanol (3.9 g, 45.3 mmol) was added dropwise at room temperature. After 1.5 h, the solvent was removed by evaporation to yield the title compound as a yellow solid (9 g) that was used in the next step without further purification. MS (EP) m/z: 362 (M++1). (Calcd. For C16H15F4NO4, 361.29)

Workup

  1. concentrationThe mixture was concentrated
  2. customdried under high vacuum for 5 hours
  3. dissolutionThe crude product was dissolved in DCM (50 mL)
  4. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-e987db7679314c53b328d8b62a40ab6b
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

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