3-Nitrophenol → HCID 18789608, compound

HRID 1106768Notes

Reaction equation

HRID 1106768 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([N:32]1[CH:36]=[C:35]([CH2:37][OH:38])[N:34]=[CH:33]1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[N+:39]([C:42]1[CH:43]=[C:44](O)[CH:45]=[CH:46][CH:47]=1)([O-:41])=[O:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[N+:39]([C:42]1[CH:47]=[C:46]([CH:45]=[CH:44][CH:43]=1)[O:38][CH2:37][C:35]1[N:34]=[CH:33][N:32]([C:13]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:36]=1)([O-:41])=[O:40]

Participants

6

Reactant 4

HCID 111373-NitrophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 382182[1-(triphenylmethyl)-1H-imidazol-4-yl]methanol

Product 1

HCID 18789608HCID 18789608, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diethyl azodicarboxylate (2.1 mL) in tetrahydrofuran (THF) (40 mL) was added (1-trityl-1H-imidazole-4-yl)methanol (2.23 g, prepared as described in J. Med. Chem. (1977)20:721) and 3-nitrophenol (2 g). To this mixture at 0° C. was added dropwise a solution of triphenyl phosphine (3.44 g) in THF (60 mL). The reaction mixture was stirred at room temperature overnight. After evaporation of the solvent the residue was chromatographed on silica gel eluting with ethyl acetate:hexane (40:60) to isolate 4-(3-nitro-phenoxymethyl)-1-trityl-1H-imidazole (2 g).

Workup

  1. customAfter evaporation of the solvent the residue
  2. customwas chromatographed on silica gel eluting with ethyl acetate:hexane (40:60)

Sources & evidence

ORD record
ord-80e870a994ca4f3a9b1df12aa1d9d298
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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