Acetic Anhydride → HCID 178471877, compound

HRID 620869Notes

Reaction equation

HRID 620869 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].[CH2:19](OC(OCC)OCC)C.C(OC(=O)C)(=O)C.[CH:36]1([NH2:39])[CH2:38][CH2:37]1>C(O)(C)C>[F:1][C:2]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[CH:12][C:3]=1[C:4]([C:6](=[CH:19][NH:39][CH:36]1[CH2:38][CH2:37]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 69828CyclopropylamineHCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate

Product 1

HCID 178471877HCID 178471877, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
150 °C

Procedure

To 10.2 g (38.5 mmol) of the 2-(2,3,4,5-tetrafluorobenzoylacetic acid, ethyl ester was added 8.4 g (57.0 mmol) of triethylorthoformate and 9.3 g (91.5 mmol) of acetic anhydride. The mixture was heated to 150° C. for two hours and was then placed under high vacuum at 75°-85° C. for one hour. The residue dissolved, without purification, in 100 ml of isopropyl alcohol and treated with 2.4 ml of cyclopropylamine. The reaction was allowed to stand overnight. It was concentrated and purified by column chromatography (silica gel 70-200, using hexane:chloroform:isopropyl alcohol, 80:15:5). The product off the column was recrystallized from pentane to give 6.16 g of 2-(2,3,4,5-tetrafluoro-benzoyl)-3-cyclopropylaminoacrylic acid, ethyl ester, mp 63°-64° C.

Workup

  1. waitto stand overnight
  2. concentrationIt was concentrated
  3. custompurified by column chromatography (silica gel 70-200, using hexane:chloroform:isopropyl alcohol, 80:15:5)
  4. customThe product off the column was recrystallized from pentane

Sources & evidence

ORD record
ord-58746a71a00e403a98a9c0b29480e597
Source dataset
uspto-grants-1989_04
Patent number
US04822801

Reaction notes

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