1-(1H-Imidazol-4-yl)-1-(naphtho[2,1-b]furan-7-yl)-2-methyl-1-propanol → HCID 178450034, compound

HRID 480468Notes

Reaction equation

HRID 480468 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([C:11]2[CH:12]=[C:13]3[C:21](=[CH:22][CH:23]=2)[C:20]2[CH:19]=[CH:18][O:17][C:16]=2[CH:15]=[CH:14]3)([OH:10])[CH:7]([CH3:9])[CH3:8])[N:3]=[CH:2]1>C(O)(=O)C.[C].[Rh]>[CH2:19]1[CH2:18][O:17][C:16]2[CH:15]=[CH:14][C:13]3[C:21]([C:20]1=2)=[CH:22][CH:23]=[C:11]([C:6]([C:4]1[N:3]=[CH:2][NH:1][CH:5]=1)([OH:10])[CH:7]([CH3:9])[CH3:8])[CH:12]=3

Participants

4

Reactant 1

HCID 1784500551-(1H-Imidazol-4-yl)-1-(naphtho[2,1-b]furan-7-yl)-2-methyl-1-propanol

Product 1

HCID 178450034HCID 178450034, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 178503043HCID 178503043, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(1H-imidazol-4-yl)-1-(naphtho[2,1-b]furan-7-yl)-2-methyl-1-propanol (0.310 g) and 5% rhodium carbon (1.50 g) in acetic acid (50 mL) was stirred at room temperature for 7 h under hydrogen atmosphere at 4 atom pressure. Catalyst was filtered off, and the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate solution and brine, dried and concentrated. The residue was chromatographed on silica gel (eluent; dichloromethane:methanol=20:1) followed by crystallization from ethyl acetate to give the titled compound (0.107 g) as a colorless solid.

Workup

  1. filtrationCatalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate solution and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (eluent; dichloromethane:methanol=20:1)
  8. customfollowed by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-ccebd620045d4243b0d1f0c44a67cd15
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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