Triphenylphosphine → HCID 22677040, compound

HRID 1837432Notes

Reaction equation

HRID 1837432 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[F:13][C:14]1[C:19]([F:20])=[C:18]([C:21]2[N:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:23][N:22]=2)[CH:17]=[CH:16][C:15]=1[OH:36].[CH3:37][Si:38]([CH3:51])([CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:51][Si:38]([CH3:37])([CH2:46][Si:47]([CH3:48])([CH3:49])[CH3:50])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][O:36][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[N:22]=[CH:23][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:25][N:26]=2)=[C:19]([F:20])[C:14]=1[F:13]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 59912411HCID 59912411, compoundHCID 135585899HCID 135585899, compound

Product 1

HCID 22677040HCID 22677040, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethylazodicarboxylate (0.087 g, 0.500 mmol) in THF (5.0 ml) was added dropwise to a stirred solution of 2,3-difluoro-4-(5-nonylpyrimidin-2-yl)-phenol (0.134 g, 0.400 mmol), compound 14 (0.108 g, 0.440 mmol) and triphenylphosphine (0.130 g, 0.500 mmol) in THF (20 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-3491e6f55ec84df69bc5f293e5ecd626
Source dataset
uspto-grants-2004_08
Patent number
US06783812B2

Reaction notes

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