Methyl 4,4,4-trifluoro-3-oxobutanoate → HCID 18942343, compound

HRID 355407Notes

Reaction equation

HRID 355407 reaction equation
[F:1][C:2]1[C:8]([OH:9])=[C:7]([F:10])[CH:6]=[CH:5][C:3]=1[OH:4].C[O:12][C:13](=O)[CH2:14][C:15]([C:17]([F:20])([F:19])[F:18])=O>>[F:10][C:7]1[CH:6]=[C:5]2[C:3](=[C:2]([F:1])[C:8]=1[OH:9])[O:4][C:13](=[O:12])[CH:14]=[C:15]2[C:17]([F:20])([F:19])[F:18]

Participants

3

Reactant 2

HCID 550266Methyl 4,4,4-trifluoro-3-oxobutanoateHCID 108445152,4-Difluororesorcinol

Product 1

HCID 18942343HCID 18942343, compoundYield 30%

Procedure

A solution of Compound 4 (0.46 g, 3.1 mmol) and methyl-4,4,4-trifluoroacetoacetate (0.55 g, 3.2 mmol) in 7 mL CH3 SO3H is stirred at 20° C. for 48 hours. The reaction mixture is poured into 70 mL ice water, and the resulting precipitate is collected by filtration, washed with water, dried in vacuo at 60° C. for 16 hours to yield 240 mg (30%) of Compound 20 as an off-white powder. 1 H-NMR (DMSO-d6) δ 7.33 (d, 1 H), 6.99 (s, 1H). 19F-NMR (DMSO-d6) Φ 59.38 (s, 3F), 129.93 (t, J=9.9 Hz, 1H), 147.78 (d, J=9.3 Hz, 1F).

Workup

  1. filtrationthe resulting precipitate is collected by filtration
  2. washwashed with water
  3. customdried in vacuo at 60° C. for 16 hours

Sources & evidence

ORD record
ord-f5f95678e9184a36bd6eb98a19db8281
Source dataset
uspto-grants-1998_11
Patent number
US05830912

Reaction notes

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