Triphenylphosphine → HCID 178444435, compound

HRID 2226081Notes

Reaction equation

HRID 2226081 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][C@H:18]3[CH2:23][CH2:22][C@H:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:20][CH2:19]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:29][CH2:30][O:31][C:32]([C@@H:34](O)[CH3:35])=[O:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:24]([C@H:21]1[CH2:20][CH2:19][C@H:18]([CH2:17][CH2:16][CH2:15][CH2:14][C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[CH:3][C:2]([O:1][C@H:34]([CH3:35])[C:32]([O:31][CH2:30][CH3:29])=[O:33])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)[CH2:23][CH2:22]1)[CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 92831(L)-ethyl lactateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178444434HCID 178444434, compound

Product 1

HCID 178444435HCID 178444435, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4 g of 4-hydroxy-4'-[4-(trans-4-pentylcyclohexyl)-1-butyl]biphenyl, 1.3 g of ethyl L(-)-lactate, 2.9 g of triphenylphosphine and 100 ml of tetrahydrofuran was treated with 1.9 g of diethyl azodicarboxylate. The reaction mixture was stirred at room temperature overnight, then concentrated and suspended with 100 ml of hot hexane. The precipitate which thereby resulted was removed by filtration and the filtrate was concentrated. Chromatography of the residue on silica gel with toluene/ethyl acetate (vol. 4:1) and recrystallization from ethanol gave 2.9 g of pure ethyl 2(R)-[4'-[4-(trans-4-pentylcyclohexyl)-1-butyl]-4-biphenylyloxy]propionate with m.p. (C-SB) 71° C. and cl.p. (SB -I) 76° C.

Workup

  1. concentrationconcentrated
  2. customThe precipitate which thereby resulted
  3. customwas removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customChromatography of the residue on silica gel with toluene/ethyl acetate (vol. 4:1) and recrystallization from ethanol

Sources & evidence

ORD record
ord-6b4757977e614baa9d2d7025f3bcb7fa
Source dataset
uspto-grants-1994_09
Patent number
US05346647

Reaction notes

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