Triphenylphosphine → 4-(Trimethylsilyl)butyl 4-(5-octyloxypyrimidin-2-yl)-phenyl ether

HRID 2226343Notes

Reaction equation

HRID 2226343 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[CH2:10]([O:18][C:19]1[CH:20]=[N:21][C:22]([C:25]2[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=2)=[N:23][CH:24]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:10]([O:18][C:19]1[CH:24]=[N:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([O:7][CH2:6][CH2:5][CH2:4][CH2:3][Si:2]([CH3:9])([CH3:8])[CH3:1])=[CH:27][CH:26]=2)=[N:21][CH:20]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2628454-(Trimethylsilyl)butan-1-olHCID 135708811Phenol, 4-[5-(octyloxy)-2-pyrimidinyl]-

Product 1

HCID 147448484-(Trimethylsilyl)butyl 4-(5-octyloxypyrimidin-2-yl)-phenyl ether

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

439 mg (3 mmol) of 4-(Trimethylsilyl)butan-1-ol and 901 mg (3 mmol) of 4-(5-n-octyloxypyrimidin-2-yl)phenol are added to the solution of 0.46 ml (3 mmol) of diethyl azodicarboxylate and 790 mg (3 mmol) of triphenylphosphine in 15 ml of dry tetrahydrofuran. After a reaction time of 15 h, the solvent is distilled off and the residue is purified chromatographically (SiO2 /CH2Cl2). After recrystallization from n-hexane, 790 mg of colorless crystals are obtained.

Workup

  1. distillationAfter a reaction time of 15 h, the solvent is distilled off
  2. customthe residue is purified chromatographically (SiO2 /CH2Cl2)
  3. customAfter recrystallization from n-hexane, 790 mg of colorless crystals
  4. customare obtained

Sources & evidence

ORD record
ord-0ca4137002b94de5b39231a9fa01d208
Source dataset
uspto-grants-1994_09
Patent number
US05348684

Reaction notes

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