Triphenylphosphine → HCID 69002236, compound

HRID 230779Notes

Reaction equation

HRID 230779 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1.O[CH2:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]([O:49][CH3:50])=[O:48])=[CH:43][CH:42]=1>C1COCC1>[N:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[O:32][CH2:40][C:41]1[CH:42]=[CH:43][C:44]([C:47]([O:49][CH3:50])=[O:48])=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 81325Methyl 4-(hydroxymethyl)benzoateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178516071HCID 178516071, compound

Product 1

HCID 69002236HCID 69002236, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triphenyl phosphine (614 mg) and a THF solution (1 mL) of diethyl azodicarboxylate (408 mg) were added in that order to a THF solution (20 mL) of 2-hydroxypyridine (149 mg) and methyl 4-hydroxymethylbenzenecarboxylate (260 mg), and stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 2/3 to ethyl acetate alone) to obtain the entitled compound (85 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 2/3 to ethyl acetate alone)

Sources & evidence

ORD record
ord-de84991e405c422890ac3f2891e3d599
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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