Acetic Anhydride → HCID 44185486, compound

HRID 2279611Notes

Reaction equation

[F:1][CH:2]([F:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:12]([O:15][C:16](=O)C)(=O)[CH3:13].C(OC(OCC)OCC)C>>[CH2:12]([O:15]/[CH:16]=[C:4](/[C:3](=[O:10])[CH:2]([F:11])[F:1])\[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:13]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 31214Ethyl orthoformate

HCID 67697Ethyl 4,4-difluoroacetoacetate

Product 1

HCID 44185486HCID 44185486, compound

Conditions

Temperature: 110 °C

Procedure

A mixture of ethyl 4,4-difluoro-3-oxobutanoate (4.65 g, 0.028 moles), acetic anhydride (8.0 g, 0.078 moles) and triethylorthoformate (7.3 g, 0.049 moles) is heated at 110° C. for 4 h. The mixture is concentrated under vacuum to afford (Z)-ethyl 2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoate as yellow oil. The oil is dissolved in EtOH (25 mL) and cooled in an ice bath. To this cooled stirred mixture is added anhydrous hydrazine (0.7 mL, 0.022 mole) and the mixture is allowed to warm gradually to RT overnight. The mixture is concentrated under vacuum and the crude product is purified by silica gel column chromatography using 1-2% MeOH/CH2Cl2 to afford the title compound as a yellow solid.

Workup

concentrationThe mixture is concentrated under vacuum

Sources & evidence

ORD record: ord-b04f98a0f5884a85b652bd58460f8cf1
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133204B2

Reaction notes

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