HCID 22388405, compound → HCID 22387947, compound

HRID 1699836Notes

Reaction equation

HRID 1699836 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[C:4]([C:6]1[C:7]2[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][C:8]=2[O:9][C:10]=1[CH3:11])=[O:5]>O1CCCC1>[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[CH:4]([OH:5])[C:6]1[C:7]2[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][C:8]=2[O:9][C:10]=1[CH3:11]

Participants

3

Reactant 1

HCID 22388405HCID 22388405, compound

Product 1

HCID 22387947HCID 22387947, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(2,4-Dichlorobenzoyl)-5-(methoxycarbonyl)-2-methylbenzo[b]furan (0.84 g, 2.31 mmol) was dissolved in tetrahydrofuran (20 ml) and a solution (1.0 M, 5 ml, 5 mmol) of a borane-tetrahydrofuran complex in tetrahydrofuran was added. The mixture was stirred at room temperature for 30 min and then at 50° C. for 2 hr. The reaction mixture was concentrated under reduced pressure and a saturated aqueous ammonium chloride solution was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure to give the objective compound (0.8 g) as a colorless oil. This crude product was used in the next reaction as it was.

Workup

  1. waitat 50° C. for 2 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiona saturated aqueous ammonium chloride solution was added to the residue
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe desiccant was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6ada02c0544f4e7584ceb17bbf827cb9
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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