2-Phenylethanol → Triphenylphosphine Oxide

HRID 1982795Notes

Reaction equation

HRID 1982795 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(CC[OH:28])C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1>[C:14]1([P:7](=[O:28])([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 60542-PhenylethanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Triphenylphosphine (1.2 g, 5.4 mmol) and 2-phenylethanol (0.65 g, 5.4 mmol) were sequentially added to a solution of tri-N2,1,2′-O-acetyl-L-biopterin (1.5 g, 4.21 mmol) in 1,4-dioxane (7 ml). To this mixture diisopropylazodicarboxylate (1.05 ml, 5.4 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 18 h. Evaporation and column chromatography on silica gel eluting with AcOEt (1:2) followed by AcOEt gave the expected product together with triphenylphosphine oxide.

Workup

  1. customEvaporation and column chromatography on silica gel eluting with AcOEt (1:2)

Sources & evidence

ORD record
ord-9a2138b605af4915820e36b725b6a4a6
Source dataset
uspto-grants-2009_06
Patent number
US07541360B2

Reaction notes

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