Triphenylphosphine → trans-2-(4-Dec-5-enyloxy-phenyl)-5-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-pyrimidine

HRID 1882750Notes

Reaction equation

HRID 1882750 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[F:13][C:14]([F:43])([C:33]([F:42])([F:41])[C:34]([F:40])([F:39])[C:35]([F:38])([F:37])[F:36])[CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[N:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[N:24][CH:25]=1.[CH2:44](O)[CH2:45][CH2:46][CH2:47]/[CH:48]=[CH:49]/[CH2:50][CH2:51][CH2:52][CH3:53].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:44]([O:32][C:29]1[CH:28]=[CH:27][C:26]([C:23]2[N:22]=[CH:21][C:20]([O:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]([F:13])([F:43])[C:33]([F:41])([F:42])[C:34]([F:39])([F:40])[C:35]([F:36])([F:37])[F:38])=[CH:25][N:24]=2)=[CH:31][CH:30]=1)[CH2:45][CH2:46][CH2:47]/[CH:48]=[CH:49]/[CH2:50][CH2:51][CH2:52][CH3:53]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 52832925-Decen-1-ol, (5E)-HCID 5462977Diethyl azodicarboxylateHCID 1355858974-[5-(5,5,6,6,7,7,8,8,8-Nonafluorooctyloxy)-pyrimidin-2-yl]-phenol

Product 1

HCID 23509149trans-2-(4-Dec-5-enyloxy-phenyl)-5-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of DEAD (0.261 g, 1.50 mmol) in THF (20) was added dropwise to a stirred solution of 4-[5-(5,5,6,6,7,7,8,8,8-nonafluorooctyloxy)-pyrimidin-2-yl]-phenol (0.693 g, 1.50 mmol), trans-5-decen-1-ol (0.234 g, 1.50 mmol) and triphenylphosphine (0.399 g, 1.50 mmol) in THF (30) and the reaction mixture stirred at room temperature for 16 h. The solvent was removed in vacuo and the residues purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1)] to yield a colorless solid, which was recrystallized from ethanol.

Workup

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

Sources & evidence

ORD record
ord-104789d05eba48a690decbce1e4e773a
Source dataset
uspto-grants-2004_07
Patent number
US06759101B2

Reaction notes

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