HCID 67885369, compound → HCID 86747308, compound

HRID 1656406Notes

Reaction equation

HRID 1656406 reaction equation
[OH:1][CH2:2][C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[N:25]([C:26]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6]([CH2:45][CH2:46][CH3:47])=[N:5][C:4]=1/[CH:48]=[CH:49]\[C:50]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH:53]=[CH:52][CH:51]=1>[O-2].[O-2].[Mn+4].C(Cl)Cl>[C:50]1(/[CH:49]=[CH:48]\[C:4]2[N:5]=[C:6]([CH2:45][CH2:46][CH3:47])[N:7]([CH2:8][C:9]3[CH:10]=[CH:11][C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:21]4[N:25]([C:26]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)([C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)[C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=5)[N:24]=[N:23][N:22]=4)=[CH:13][CH:14]=3)[C:3]=2[CH:2]=[O:1])[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH:53]=[CH:52][CH:51]=1

Participants

4

Reactant 1

HCID 67885369HCID 67885369, compound

Product 1

HCID 86747308HCID 86747308, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

5-Hydroxymethyl-4-[cis-(naphth-1-yl)ethenyl]-2-n-propyl-1-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]imidazole (7.86 g, 10.2 mmol, 1 eq), manganese dioxide (4.44 g, 51.1 mmol, 5 eq), and methylene chloride (25 mL) were mixed and refluxed under N2 overnight. The manganese dioxide was filtered through Celite™ and the cake washed with methylene chloride. The filtrate was evaporated, and the residue flash chromatographed in 75:25 pentane/ethyl acetate to 1:1 pentane/ethyl acetate to yield 3.78 g of an orange lass. NMR (CDCl3) δ 9.37 (s, 1H); 8.04 (m, 1H); 7.92 (d, 1H, J=8 Hz); 7.80 (m, 1H); 7.72 (m, 1H); 7.60-7.10 (m, 16H); 7.10-6.70 (m, 10H); 6.53 (d, 2H, J=8 Hz); 5.30 (s, 2H); 2.38 (t, 2H, J=7 Hz); 1.56 (t of q, 2H, J=7,7 Hz); 0.77 (t, 3H, J=7 Hz). Anal. calcd. for C52H42N6O.(H2O)0.7 : C, 80.12; H, 5.61; N, 10.78. Found: C, 80.24; H, 5.91; N, 10.46. ##STR222##

Workup

  1. temperaturerefluxed under N2 overnight
  2. filtrationThe manganese dioxide was filtered through Celite™
  3. washthe cake washed with methylene chloride
  4. customThe filtrate was evaporated
  5. customthe residue flash chromatographed in 75:25 pentane/ethyl acetate to 1:1 pentane/ethyl acetate
  6. customto yield 3.78 g of an orange lass

Sources & evidence

ORD record
ord-10b912395bca49238f3aa18396eee023
Source dataset
uspto-grants-1993_10
Patent number
US05254546

Reaction notes

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