Triphenylphosphine → 2-[4-[(3E)-3-Hepten-1-yloxy]phenyl]-5-[(5,5,6,6,7,7,8,8,8-nonafluorooctyl)oxy]pyrimidine

HRID 1882751Notes

Reaction equation

HRID 1882751 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]/[CH:46]=[CH:47]/[CH2:48][CH2:49][CH3:50].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]/[CH:46]=[CH:47]/[CH2:48][CH2:49][CH3:50]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 53180183-Hepten-1-ol, (3E)-HCID 5462977Diethyl azodicarboxylateHCID 1355858974-[5-(5,5,6,6,7,7,8,8,8-Nonafluorooctyloxy)-pyrimidin-2-yl]-phenol

Product 1

HCID 235091502-[4-[(3E)-3-Hepten-1-yloxy]phenyl]-5-[(5,5,6,6,7,7,8,8,8-nonafluorooctyl)oxy]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of DEAD (0.261 g, 1.50 mol) 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-3-hepten-1-ol (0.171 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-8ff2a0bc534d48aab725d0efd3080df0
Source dataset
uspto-grants-2004_07
Patent number
US06759101B2

Reaction notes

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