Triphenylphosphine → HCID 67824263, compound

HRID 1728270Notes

Reaction equation

HRID 1728270 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([OH:22])=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH3:3].[CH2:23](O)[CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH3:30].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH3:30])=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53645193-Octen-1-ol, (3Z)-HCID 190171892-[4-(5-[Propyloxy]-1-pentyl)phenyl]-5-hydroxypyrimidine

Product 1

HCID 67824263HCID 67824263, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.5 g of 2-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-hydroxypyrimidine, 0.3 g of (Z)-3-octen-1-ol, 0.4 g of diethyl azodicarboxylate, 0.6 g of triphenylphosphine and 25 ml of absolute tetrahydrofuran was stirred at room temperature overnight and then concentrated. The residue was suspended with 50 ml of hot hexane and filtered. The filtrate was concentrated. Chromatography of the residue on silica gel with toluene/hexane (vol. 1:1) and recrystallization from methanol gave pure 2-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-([(Z)-3-octenyl]oxy)pyrimidine, m.p. (C-I) 38° C.

Workup

  1. concentrationconcentrated
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customChromatography of the residue on silica gel with toluene/hexane (vol. 1:1) and recrystallization from methanol

Sources & evidence

ORD record
ord-fc01e8eeb335460ebfb2623ae924a12d
Source dataset
uspto-grants-1994_07
Patent number
US05326497

Reaction notes

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