2-Methyl-2-butene → 4-[4-(Trifluoromethyl)phenyl]thiophene-2-carboxylic acid

HRID 9640

Reaction equation

HRID 9640 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:14]=[O:15])[S:12][CH:13]=2)=[CH:5][CH:4]=1.CC(=CC)C.Cl([O-])=[O:24].[Na+].P([O-])(O)(O)=O.[Na+]>O.C(O)(C)(C)C>[F:17][C:2]([F:16])([F:1])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]([C:14]([OH:24])=[O:15])[S:12][CH:13]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 117369544-(4-Trifluoromethylphenyl)thiophene-2-carbaldehyde2×HCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 219865124-[4-(Trifluoromethyl)phenyl]thiophene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 4-[4-(trifluoromethyl)phenyl]thiophene-2-carbaldehyde (intermediate 37, 1.23 g), t-butanol (20 ml) and 2-methyl-2-butene (10 ml) was cooled to 0° C. To this was added drop-wise, a solution of sodium chlorite (3.8 g) and sodium dihydrogen phosphate (4.03 g) in water (15 ml). After the addition was complete, the mixture was allowed to warm to room temperature and was stirred for 4 hours. The solution was then concentrated and partitioned between water and ethyl acetate. The aqueous layer was washed with a second ethyl acetate portion and the organic liquors were combined, washed with brine, then dried (MgSO4). The solution was then absorbed onto silica and loaded onto a SPE (Si) cartridge. The product was eluted with neat ethyl acetate to afford the title compound as a white solid.

Workup

  1. additionTo this was added drop-wise
  2. additionAfter the addition
  3. concentrationThe solution was then concentrated
  4. custompartitioned between water and ethyl acetate
  5. washThe aqueous layer was washed with a second ethyl acetate portion
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customThe solution was then absorbed onto silica
  9. washThe product was eluted with neat ethyl acetate

Sources & evidence

ORD record
ord-6f39bd3263d74268b672227e11e8ee23
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Linked notes

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