Acetic Anhydride → HCID 178471956, compound

HRID 1396092Notes

Reaction equation

HRID 1396092 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].CC(O[C:23]([CH3:25])=[O:24])=O.[CH:26](OCC)(OCC)OCC.[NH2:36][C:37]1(C(O)C)[CH2:39][CH2:38]1>C1(C)C=CC=CC=1>[OH:24][CH2:23][CH2:25][C:37]1([NH:36][CH:26]=[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])[CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoateHCID 669351111903318-44-4

Product 1

HCID 178471956HCID 178471956, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate (3.09 g, 11.7 mmol), Ac2O (6.7 mL, 70.9 mmol) and triethyl orthoformate (3.90 mL, 23.5 mmol) was heated at 120° C. for 3 hours. The mixture was concentrated in vacuo and dried under high vacuum. The crude product was dissolved in anhydrous tolene (40 mL) and (1-amino-cyclopropyl)-ethanol (1.82 g, 11.7 mmol) was added very slowly at 0° C. The ration mixture was stirred at room temperature for 5 hours and diluted with toluene. The organic layer was washed with water, brine, and then dried. The solvent was removed by evaporation and the crude product was purified by column chromatography (Hexane:EtOAc 2:1→1:1) to yield the title compound (2.99 g, 68%) as a yellow oil. 1H-NMR (400 MHz, CDCl3) δ 0.85-0.92 (2H, m), 0.94-1.11 (5H, m), 1.85-1.91 (2H, m), 3.85-3.89 (2H, m), 3.99-4.09 (2H, m), 6.95-7.13 (1H, m), 8.19 (1H, d, J=14.1 Hz), 9.84, 11.2 (each d, J=13.4 Hz, total 1H). EIMS (+) 375 [M]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customdried under high vacuum
  3. additionwas added very slowly at 0° C
  4. washThe organic layer was washed with water, brine
  5. customdried
  6. customThe solvent was removed by evaporation
  7. customthe crude product was purified by column chromatography (Hexane:EtOAc 2:1→1:1)

Sources & evidence

ORD record
ord-90b6ae75a0d146b5a79df6cd25d66554
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

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