Triphenylphosphine → HCID 14178011, compound

HRID 2352135Notes

Reaction equation

HRID 2352135 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][C:36]([C:39]2[N:44]=[CH:43][C:42]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])=[CH:41][N:40]=2)=[CH:35][CH:34]=1.[O:54]1[C@@H:57]([CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[C@@H:55]1[CH3:56]>O1CCCC1>[CH2:45]([C:42]1[CH:43]=[N:44][C:39]([C:36]2[CH:35]=[CH:34][C:33]([O:32][CH2:56][C@H:55]3[C@H:57]([CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[O:54]3)=[CH:38][CH:37]=2)=[N:40][CH:41]=1)[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11007921HCID 11007921, compoundHCID 1358247454-(5-Nonyl-2-pyrimidinyl)phenol

Product 1

HCID 14178011HCID 14178011, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.31 g (5 mmol) of triphenyl phosphine and 0.79 g (5 mmol) of diethyl azodicarboxylate are combined in 10 ml of tetrahydrofuran at 0° C. After 20 minutes, 1.49 g (5 mmol) of 2-(4-hydroxyphenyl)-5-n-nonylpyrimidine and 0.72 g (5 mmol) of (2S,3S)-2,3-epoxyoctane, each in 8 ml of tetrahydrofuran, are added. After 24 hours, the mixture is evaporated to dryness in vacuo, and the residue is chromatographed on silica gel (200 g) using CH2Cl2. After recrystallization from hexane, 0.79 g of colorless crystals is obtained; (α) D25 : -15.3° (c=5,CHCl3)

Workup

  1. waitAfter 24 hours
  2. customthe mixture is evaporated to dryness in vacuo
  3. customthe residue is chromatographed on silica gel (200 g)
  4. customAfter recrystallization from hexane

Sources & evidence

ORD record
ord-876e505c9b664ba4a18b644c0b95eac4
Source dataset
uspto-grants-1989_10
Patent number
US04876028

Reaction notes

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