p-Diiodobenzene → 1-(4-Benzyloxy-phenyl)-1-(4-iodophenyl)-2-phenyl-butan-1-ol

HRID 2393586Notes

Reaction equation

HRID 2393586 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][CH:3]=1.C([Li])CCC.[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:38])[CH:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:30][CH3:31])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)C>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([C:2]2[CH:7]=[CH:6][C:5]([I:8])=[CH:4][CH:3]=2)([OH:38])[CH:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:30][CH3:31])=[CH:24][CH:23]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 12208p-DiiodobenzeneHCID 25517Ammonium ChlorideHCID 189765134-Benzyloxy-alpha-ethyldesoxybenzoinHCID 178418339Butyllithium

Product 1

HCID 189764571-(4-Benzyloxy-phenyl)-1-(4-iodophenyl)-2-phenyl-butan-1-olYield 108.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 23.4 g of 1,4-diiodobenzene in 124 ml of tetrahydrofuran is mixed drop by drop at -70° C. under nitrogen with 45 ml of a 1.6 molar butyllithium solution, and it is stirred for 5 more minutes. Then, a solution of 18 g of 1-(4-benzyloxy-phenyl)-2-phenyl-butan-1-one [D. W. Robertson; J. A. Katzenellenbogen; D. J. Ellen; A. Rorke; B. S. Katzenellenbogen, J. Steroid Biochem., 1982, 16, 1-13] in 180 ml of tetrahydrofuran is added in drops, allowed to come to room temperature by completing the cooling, and it is stirred for 1 more hour. For working-up, 60 ml of saturated ammonium chloride solution is added, diluted with diethyl ether, washed neutral with water, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with pentane/diethyl ether. 31.5 g of 1-(4-benzyloxy-phenyl)-1-(4-iodophenyl)-2-phenyl-butan-1-ol is obtained as oil.

Workup

  1. customto come to room temperature
  2. stirringis stirred for 1 more hour
  3. washwashed neutral with water
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customchromatographed on silica gel with pentane/diethyl ether

Sources & evidence

ORD record
ord-ebe11cd1f0354c55aa6b82c1043a222f
Source dataset
uspto-grants-1998_09
Patent number
US05807899

Reaction notes

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