2,5-Dimethoxytetrahydrofuran → 276861-97-3

HRID 1375024Notes

Reaction equation

HRID 1375024 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].CO[CH:17]1[CH2:21][CH2:20][CH:19](OC)O1>C(O)(=O)C.O1CCOCC1>[N:1]1([C:2]2[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=2)[C:5]([OH:7])=[O:6])[CH:17]=[CH:21][CH:20]=[CH:19]1

Participants

5

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 6095563-Amino-5-(trifluoromethyl)benzoic acid

Product 1

HCID 17963985276861-97-3

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-amino-5-(trifluoromethyl)benzoic acid (2.0 g) and 2,5-dimethoxytetrahydrofuran (1.52 ml) in a mixture of acetic acid (10 ml) and 1,4-dioxane (10 ml) was stirred at 100° C. for 2 hours. After cooling to room temperature, the mixture was concentrated and purified with column chromatography (silica gel, 50 ml, methanol:dichloromethane=10:90) to give crude solid. The solid was recrystallized from ethyl acetate (5.0 ml) and hexane (200 ml) to give 3-(pyrrol-1-yl)-5-(trifluoromethyl)-benzoic acid (1.72 g) as a powder.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated
  3. custompurified with column chromatography (silica gel, 50 ml, methanol:dichloromethane=10:90)
  4. customto give crude solid
  5. customThe solid was recrystallized from ethyl acetate (5.0 ml) and hexane (200 ml)

Sources & evidence

ORD record
ord-af743b003de44395b8957aecbe70c1b3
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

Loading…