Potassium Hydroxide → HCID 53721853, compound

HRID 1197129Notes

Reaction equation

HRID 1197129 reaction equation
[OH-].[K+].[CH2:3]1[C:16]2[CH:15]=[CH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[C:6](=[O:17])[CH2:5][CH2:4]1.[CH3:18][C:19]1[N:23]([C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:22]=[N:21][C:20]=1[CH:43]=O>CO>[CH3:18][C:19]1[N:23]([C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:22]=[N:21][C:20]=1[CH:43]=[C:5]1[C:6](=[O:17])[C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:14]=[CH:15][C:16]=2[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 2404612,3-Dihydro-1H-phenanthren-4-oneHCID 118243385-methyl-1-trityl-1H-imidazole-4-carbaldehyde

Product 1

HCID 53721853HCID 53721853, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of potassium hydroxide (0.25 g) in methanol (5 ml) was added to a solution of 1,2-dihydro-4(3H)-phenanthrenone (0.5 g) and 5-methyl-1-(triphenylmethyl)-1H-imidazole-4-carboxaldehyde (0.9 g) in methanol (20 ml). The mixture was kept at 23° for 5 days after which time a solid had separated. This was filtered off, washed with ethanol and purified by FCC eluting firstly with hexane/dichloromethane (1:1) and then with dichloromethane to give the title compound (0.86 g), m.p. 145°-148° (decomp.).

Workup

  1. customafter which time a solid had separated
  2. filtrationThis was filtered off
  3. washwashed with ethanol
  4. custompurified by FCC
  5. washeluting firstly with hexane/dichloromethane (1:1)

Sources & evidence

ORD record
ord-1d35930cbf7246909252369ba5529112
Source dataset
uspto-grants-1992_05
Patent number
US05116984

Reaction notes

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