Triphenylphosphine → HCID 22677037, compound

HRID 1837433Notes

Reaction equation

HRID 1837433 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH2:13]([C:21]1[CH:22]=[N:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=[N:25][CH:26]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[CH3:34][Si:35]([CH3:51])([CH2:45][CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:51][Si:35]([CH3:34])([CH2:45][CH2:46][Si:47]([CH3:48])([CH3:49])[CH3:50])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][O:33][C:30]1[CH:31]=[CH:32][C:27]([C:24]2[N:23]=[CH:22][C:21]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:26][N:25]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 6040552-(4-Hydroxyphenyl)-5-octylpyrimidineHCID 5462977Diethyl azodicarboxylateHCID 22677029HCID 22677029, compound

Product 1

HCID 22677037HCID 22677037, 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-octylpyrimidin-2-yl)-phenol (0.085g, 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-7dcabef7aa8f4f70b8b88241b43c3cd9
Source dataset
uspto-grants-2004_08
Patent number
US06783812B2

Reaction notes

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