Acetic Anhydride → HCID 44185486, compound

HRID 241426Notes

Reaction equation

HRID 241426 reaction equation
[C:1]([O:4][C:5](=O)C)(=O)[CH3:2].[F:8][CH:9]([F:18])[C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(OCC)(OCC)OCC>>[CH2:1]([O:4]/[CH:5]=[C:11](/[C:10](=[O:17])[CH:9]([F:18])[F:8])\[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:2]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 67697Ethyl 4,4-difluoroacetoacetate

Product 1

HCID 44185486HCID 44185486, compoundYield 86%

Conditions

Temperature
95 °C

Procedure

Add acetic anhydride (166 kg, 1625 mol) to a mixture of ethyl 4,4-difluoroacetoacetate (33 kg, 199 mol) and triethyl orthoformate (60 kg, 407 mol) maintained at 90-100° C. Stir the mixture at 90-100° C. for 8.5 hours and remove ethyl acetate using a Dean-Stark apparatus. Concentrate the reaction mixture to give the title compound (37.8 kg, 86% yield, 97% GC purity). 1H NMR (500 MHz, CDCl3,) δ 7.88 (d, J=6 Hz, 1H), 6.3 (m, 1H), 4.3 (m, 4H), 1.4 (m, 3H), 1.32 (m, 3H).

Workup

  1. customremove ethyl acetate using a Dean-Stark apparatus
  2. concentrationConcentrate the reaction mixture

Sources & evidence

ORD record
ord-2f31eeba3ae24037aa384e57ebfa7c2f
Source dataset
uspto-grants-2014_02
Patent number
US08648200B2

Reaction notes

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