Tetrahydrofuran → HCID 18351660, compound

HRID 430769Notes

Reaction equation

HRID 430769 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([C:12](O)=O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[C:15]1([CH2:21][CH2:22][C:23](=[O:26])[CH2:24][OH:25])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(N=C=NC2CCCCC2)CCCCC1.C1C[O:45][CH2:44]C1>>[C:15]1([CH2:21][CH2:22][C:23](=[O:26])[CH2:24][O:25][C:44]([CH2:12][C:8]2[C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=3[O:10][CH:9]=2)=[O:45])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 128446037-methoxy-1-benzofuran-3-carboxylic acidHCID 150904631-Hydroxy-4-phenylbutan-2-one

Product 1

HCID 18351660HCID 18351660, compoundYield 47%

Procedure

7-methoxybenzofuran-3-carboxylic acid (220 mg) was dissolved in THF (5 ml). To this solution, 4-phenyl-2-oxo-1-butanol (211 mg) and dicyclohexylcarbodiimide (330 mg) were added and the resulting solution was stirred at room temperature for 16 hours. The reaction solution was filtered and the filtrate was poured into water layer (50 ml), followed by extraction twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1) using silica gel to obtain the desired compound (178 mg, yield: 47%).

Workup

  1. filtrationThe reaction solution was filtered
  2. additionthe filtrate was poured into water layer (50 ml)
  3. extractionfollowed by extraction twice with ethyl acetate (20 ml)
  4. washwashed with saturated brine
  5. dry with materialby drying over sodium sulfate
  6. customAfter removing the sodium sulfate
  7. filtrationby filtration
  8. customthe solvent was removed under reduced pressure
  9. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-3899f041d5c7434fa90e5f89861b1b1a
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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