2,2,2-Trifluoroethanol → Methyl 3-(4-hydroxyphenyl)-2-(2,2,2-trifluoroethoxy)propanoate

HRID 1004201Notes

Reaction equation

HRID 1004201 reaction equation
[N+](=[C:3]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5])=[N-].[F:16][C:17]([F:21])([F:20])[CH2:18][OH:19]>CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[OH:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH:3]([O:19][CH2:18][C:17]([F:21])([F:20])[F:16])[C:4]([O:6][CH3:7])=[O:5])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 64092,2,2-Trifluoroethanol2×HCID 54320834Methyl 2-diazo-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 10858799Methyl 3-(4-hydroxyphenyl)-2-(2,2,2-trifluoroethoxy)propanoate

Reagents, catalysts & solvents 1

HCID 423677Acetic acid, rhodium salt (4:2)Catalyst

Procedure

A solution of methyl 2-diazo-3-(4hydroxyphenyl)propanoate (3.00 g) in 2,2,2-trifluoroethanol (10 mL) was slowly added, over 15 minutes, to a stirred mixture of rhodium (II) acetate dinner (0.064 g) and 2,2,2-trifluoroethanol (5 mL) at room temperature under a nitrogen atmosphere. The mixture was stirred at temperature for 15 minutes, then heated at reflux for 4 hours, cooled and evaporated. The residue was chromatographed on silica gel with 4% ethyl acetate in dichloromethane to afford the title compound, a gum, which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. temperaturecooled
  4. customevaporated
  5. customThe residue was chromatographed on silica gel with 4% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-5014b261f5854e2b88c156e4fe5d566e
Source dataset
uspto-grants-2000_04
Patent number
US06048883

Reaction notes

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