Triphenylphosphine → HCID 131720070, compound

HRID 263680Notes

Reaction equation

HRID 263680 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:12]/[CH:13]=[CH:14]/[C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[C@@H:9](O)[CH3:10])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P([N:70]=[N+:71]=[N-:72])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[N-:70]=[N+:71]=[N-:72].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:9][CH3:10])[CH2:12][CH:13]=[CH:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 70281683HCID 70281683, compound

Product 1

HCID 131720070HCID 131720070, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.81 g of the alcohol thus obtained was dissolved in 18 ml of tetrahydrofuran, and 2.11 g of triphenylphosphine, 1.27 ml of diethyl azodicarboxylate and 1.73 g of diphenylphosphoryl azide were added under cooling with ice under stirring, followed by stirring at room temperature for 30 minutes. The reaction solution was evaporated to dryness under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/1) to obtain 1.59 g of (4S*,5S*,5E)-5-azide-4-(4-chlorophenyl)-1-(2-naphthyl)-1-hexene.

Workup

  1. temperatureunder cooling with ice
  2. stirringby stirring at room temperature for 30 minutes
  3. customThe reaction solution was evaporated to dryness under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/1)

Sources & evidence

ORD record
ord-eb4b1b32ba174081a5fc0a5c8c220bdf
Source dataset
uspto-grants-1997_07
Patent number
US05643958

Reaction notes

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