HCID 131732997, compound → HCID 90418226, compound

HRID 2177155Notes

Reaction equation

HRID 2177155 reaction equation
[F:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([O:12][CH3:13])[CH:5]=[CH:4][C:3]=1/[CH:14]=[CH:15]\[C:16]([O:18][CH2:19][CH3:20])=[O:17]>[C].[Pd].CO>[F:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([O:12][CH3:13])[CH:5]=[CH:4][C:3]=1[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 1

HCID 131732997HCID 131732997, compound

Product 1

HCID 90418226HCID 90418226, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

Into a 50-mL round-bottom flask, was placed ethyl (2Z)-3-[2-fluoro-4-methoxy-3-(trifluoromethyl)phenyl]prop-2-enoate (200 mg, 0.68 mmol, 1.00 equiv), Palladium carbon (300 mg), methanol (15 mL). The solution was subjected to 2 atm of H2. The resulting solution was stirred overnight at 30° C. The reaction progress was monitored by LCMS. The solids were collected by filtration. The resulting mixture was concentrated under vacuum. This resulted in 0.21 g of ethyl 3-[2-fluoro-4-methoxy-3-(trifluoromethyl)phenyl]propanoate as yellow oil. Mass spectrum (ESI, m/z): Calcd. for C13H14F4O3, 295.1 (M+H). found 295.1.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. filtrationThe solids were collected by filtration
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThis resulted in 0.21 g of ethyl 3-[2-fluoro-4-methoxy-3-(trifluoromethyl)phenyl]propanoate as yellow oil

Sources & evidence

ORD record
ord-8f0c298ede124efb91490207ad9bca1a
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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