Potassium Hydroxide → HCID 22041394, compound

HRID 460300Notes

Reaction equation

HRID 460300 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:16]2[CH:21]=[C:20]([CH:22]=[O:23])[CH:19]=[CH:18][C:17]=2[O:24][C:25]([F:28])([F:27])[F:26])[C:8]2[O:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9]=2[CH:15]=1)=[O:4].[OH-].[K+]>CO>[CH:22]([C:20]1[CH:19]=[CH:18][C:17]([O:24][C:25]([F:26])([F:27])[F:28])=[C:16]([C:7]2[C:8]3[O:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9]=3[CH:15]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)[CH:21]=1)=[O:23]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86591140HCID 86591140, compound

Product 1

HCID 22041394HCID 22041394, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-(5-Formyl-2-trifluoromethoxy-phenyl)-3,3-dimethyl-2,3-dihydro-benzofuran-5-carboxylic acid methyl ester (1.76 g, 4.82 mmol) (example 8) and 5N potassium hydroxide (2 mL) in methanol (20 mL) was heated at reflux for 1 hour. The solvent was then evaporated. The mixture was diluted with water and washed twice with diethyl ether. The aqueous layers were acidified with 1N HCl and extracted twice with ethyl acetate. The organic combined extract was further washed with water, brine, dried (MgSO4), filtered and evaporated. The residue was chromatographed on silica gel (30% ethyl acetate in hexane) to afford 112 mg of 7-(5-formyl-2-trifluoromethoxy-phenyl)-3,3-dimethyl-2,3-dihydro-benzofuran-5-carboxylic acid. 10% yield. 1H-NMR (300 MHz, CDCl3): 1.43 (s, 6H), 4.36 (s, 2H), 7.51 (d, J=8.2 Hz, 1H), 7.92–8.04 (m, 4H), 10.05 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customThe solvent was then evaporated
  4. additionThe mixture was diluted with water
  5. washwashed twice with diethyl ether
  6. extractionextracted twice with ethyl acetate
  7. extractionThe organic combined extract
  8. washwas further washed with water, brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was chromatographed on silica gel (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-46ac7bf5cd3245608288528abc72fb02
Source dataset
uspto-grants-2007_03
Patent number
US07196108B2

Reaction notes

Loading…