Triphenylphosphine → HCID 66862942, compound

HRID 254924Notes

Reaction equation

HRID 254924 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@H:12]([O:24][CH2:25][O:26][CH3:27])[C@H:13]([OH:23])[CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[C:7]([O:10][CH3:11])[C:8]=1[CH3:9].[CH3:28][O:29][C:30](=[O:46])[C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][C:32]=1[O:38][C:39]1[CH:44]=[CH:43][C:42](O)=[CH:41][CH:40]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:28][O:29][C:30](=[O:46])[C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][C:32]=1[O:38][C:39]1[CH:40]=[CH:41][C:42]([O:23][C@H:13]([C@@H:12]([C:5]2[CH:6]=[C:7]([O:10][CH3:11])[C:8]([CH3:9])=[C:3]([O:2][CH3:1])[CH:4]=2)[O:24][CH2:25][O:26][CH3:27])[CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23138040HCID 23138040, compoundHCID 69492328HCID 69492328, compound

Product 1

HCID 66862942HCID 66862942, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (4 ml) solution of (±)-(1R*,2R*)-1-(3,5-dimethoxy-4-methylphenyl)-1-(methoxymethoxy)-5-phenylpentan-2-ol (142 mg) and methyl2-(4-hydroxyphenoxy)-4-methylbenzoate (249 mg), triphenylphosphine (262 mg) and diethyl azodicarboxylate (0.47 ml) were added, followed by stirring at room temperature overnight. The reaction mixture was concentrated, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain the title compound (128 mg) having the following physical properties.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-94ba09964bfd445b9bca439d4fd42664
Source dataset
uspto-grants-2011_01
Patent number
US07875745B2

Reaction notes

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