Tetrahydrofuran → HCID 11830959, compound

HRID 397059Notes

Reaction equation

HRID 397059 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=O.[C:12](P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH2:15][CH3:16])=[O:13].[OH-].[Na+].[CH2:38]1COCC1>O>[CH2:15]([O:14][C:12](/[CH:38]=[CH:1]/[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[O:13])[CH3:16]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 120884-Formylbenzoic acidHCID 14798Sodium HydroxideHCID 178473672HCID 178473672, compound

Product 1

HCID 11830959HCID 11830959, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred solution of 4-formyl-benzoic acid (10.0 g, 66.7 mmol) in THF (140 ml) was added carboethoxytriphenylphosphorane (25.0 g, 71.8 mmol). To this solution was added NaOH (2.50 g, 66.7 mmol) as a solution in water (20 ml). The reaction was stirred at rt overnight. The reaction mixture was diluted with water (50 ml) and extracted with EtOAc (3×50 ml). The combined extracts were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, 5% MeOH/CH2Cl2) to give the desired compound as a white solid (11.68 g, 53.1 mmol, 80% yield).

Workup

  1. extractionextracted with EtOAc (3×50 ml)
  2. dry with materialThe combined extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (SiO2, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-46a0ac57e7c143718c004ac8116f8be7
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

Loading…