Ethyl orthoformate → HCID 117611668, compound

HRID 2202126Notes

Reaction equation

HRID 2202126 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[CH2:16]([O:18][CH:19](OCC)OCC)[CH3:17]>C(OC(=O)C)(=O)C>[CH2:16]([O:18]/[CH:19]=[C:8](\[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)/[C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:17]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 10081833HCID 10081833, compound

Product 1

HCID 117611668HCID 117611668, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of ethyl 3-(4-fluorophenyl)-2-oxopropanoate (4 g, 19.03 mmol, 1.00 equiv) and triethoxymethane (16 mL) in acetic anhydride (5 mL) was stirred at 130° C. overnight. The reaction mixture was cooled to room temperature and then concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-10% of ethyl acetate in petroleum ether to give 700 mg (14%) of (E)-ethyl 4-ethoxy-3-(4-fluorophenyl)-2-oxobut-3-enoate as a yellow oil. 1H-NMR (300 MHz, DMSO-d6): δ 7.71 (s, 1H), 7.32-7.28 (m, 2H), 7.09-7.05 (m, 2H), 4.23 (q, J=7.0 Hz, 2H), 4.16 (q, J=8.0 Hz, 2H), 1.37-1.20 (m, 6H) ppm.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified on a silica gel column
  3. washeluted with 0-10% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-e6f273b9a7734bddba2991084e5e2249
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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