Triphenylphosphine → HCID 22677053, compound

HRID 1837434Notes

Reaction equation

HRID 1837434 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH2:13]([C:23]1[CH:24]=[N:25][C:26]([C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=2)=[N:27][CH:28]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[CH3:36][Si:37]([CH3:53])([CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:13]([C:23]1[CH:24]=[N:25][C:26]([C:29]2[CH:30]=[CH:31][C:32]([O:35][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][Si:37]([CH3:53])([CH3:36])[CH2:47][CH2:48][Si:49]([CH3:50])([CH3:51])[CH3:52])=[CH:33][CH:34]=2)=[N:27][CH:28]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 22677029HCID 22677029, compoundHCID 135585902Phenol, 4-(5-decyl-2-pyrimidinyl)-

Product 1

HCID 22677053HCID 22677053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethylazodicarboxylate (0.065 g, 0.375 mmol) in THF (5.0 ml) was added dropwise to a stirred solution of 4-(5-decylpyrimidin-2-yl)-phenol (0.094 g, 0.300 mmol), compound 17 (0.083 g, 0.300 mmol) and triphenylphosphine (0.098 g, 0.375 mmol) in THF (10 ml). The treaction mixture was stirred at room temperature for 24 h, the solvent removed in vacuo and the residues purified by column chromatography [silica gel eluted with hexane/ethyl acetate (9:1)] to yield a colorless solid that was recrystallized from acetonitrile.

Workup

  1. customthe solvent removed in vacuo
  2. customthe residues purified by column chromatography [silica gel eluted with hexane/ethyl acetate (9:1)]
  3. customto yield a colorless solid
  4. customthat was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c68b1359fae44f7b9a0c0b6366f3d40f
Source dataset
uspto-grants-2004_08
Patent number
US06783812B2

Reaction notes

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