Water → {4-[3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-phenyl}-methanol

HRID 623665

Reaction equation

HRID 623665 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([N:23]=[N+:24]=[N-:25])=[CH:11][C:10]=1[CH:26]([CH3:28])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([C:31]1[CH:36]=[CH:35][C:34]([CH2:37][OH:38])=[CH:33][CH:32]=1)#[CH:30].CCOC(C)=O.O>CN(C=O)C>[CH2:16]([O:15][C:13]1[CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10]([CH:26]([CH3:28])[CH3:27])=[CH:11][C:12]=1[N:23]1[C:29]([C:31]2[CH:36]=[CH:35][C:34]([CH2:37][OH:38])=[CH:33][CH:32]=2)=[CH:30][N:25]=[N:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11170993(4-Ethynylphenyl)methanolHCID 715342021,5-Bis-benzyloxy-2-isopropyl-4-azido-benzene

Product 1

HCID 67985193{4-[3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-phenyl}-methanolYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,5-bis-benzyloxy-2-isopropyl-4-azido-benzene (890 mg, 2.38 mmol) was dissolved in DMF (5 ml) and (4-ethynylphenyl)-methanol (286 mg, 2.16 mmol) was added at RT. The flask was subjected to three vacuum-nitrogen cycles. [Cp*RuCl]4 was then added (116 mg, 0.11 mmol) and three further cycles were done. The reaction was left to RT until completion (monitored by TLC). AcOEt and water were then added. The organic phase was extracted four times with AcOEt, washed with water (three times) and brine (one time) and dried over Na2SO4; the solvent was removed under reduced pressure and the mixture was purified by column chromatography (PE/AcOEt: 60:40). The title compound was obtained as an oil.

Workup

  1. waitThe reaction was left to RT until completion (monitored by TLC)
  2. extractionThe organic phase was extracted four times with AcOEt
  3. washwashed with water (three times) and brine (one time)
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed under reduced pressure
  6. customthe mixture was purified by column chromatography (PE/AcOEt: 60:40)

Sources & evidence

ORD record
ord-90c29a7e56c844fa858f240026d10232
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Linked notes

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