Acetic Anhydride → HCID 178472004, compound

HRID 561168Notes

Reaction equation

HRID 561168 reaction equation
[F:1][C:2]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[CH:12][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[CH3:19]C(OC(C)=O)=O.C(OCC)(OCC)OCC.[NH2:36][CH2:37][CH2:38][CH2:39][CH2:40][OH:41]>>[OH:41][CH2:40][CH2:39][CH2:38][CH2:37][NH:36][CH:19]=[C:6]([C:4](=[O:5])[C:3]1[CH:12]=[C:13]([F:18])[C:14]([F:17])=[C:15]([F:16])[C:2]=1[F:1])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 258684-Amino-1-butanolHCID 31214Ethyl orthoformateHCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate

Product 1

HCID 178472004HCID 178472004, compoundYield 97.2%

Conditions

Temperature
130 °C

Procedure

A mixture of ethyl 2,3,4,5-tetrafluorobenzoylacetate (2.64 g, 10.0 mmol), Ac2O (2.36 mL, 25.0 mmol) and triethyl orthoformate (2.49 mL, 15.0 mmol) was stirred at 130° C. for 3 h. The mixture was concentrated in vacuo and dried under high vacuum. The crude product was dissolved in EtOH (50 mL) and 4-amino-1-butanol (0.972 mL, 10.5 mmol) was added. After stirred at room temperature for 17 h, the mixture was concentrated in vacuo and the crude product was purified by column chromatography (Hexane:EtOAc 2:1→1:2) to yield ethyl 3-(4-hydroxybutylamino)-2-(2,3,4,5-tetrafluorobenzoyl)acrylate (3.53 g, 97%) as a pale yellow solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customdried under high vacuum
  3. dissolutionThe crude product was dissolved in EtOH (50 mL)
  4. stirringAfter stirred at room temperature for 17 h
  5. concentrationthe mixture was concentrated in vacuo
  6. customthe crude product was purified by column chromatography (Hexane:EtOAc 2:1→1:2)

Sources & evidence

ORD record
ord-5fce5efe24684caaa2bfa9a38084cc0c
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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