Triphenylphosphine → Triphenylphosphine Oxide

HRID 987136Notes

Reaction equation

HRID 987136 reaction equation
[OH:1]C1C=CC(CC(CC)C(OC)=O)=CC=1.CS(C1C=CC(CCO)=CC=1)(=O)=O.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.[C:47]1([P:53]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>ClCCl>[C:60]1([P:53](=[O:1])([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 22988421Methyl 2-(4-hydroxybenzyl)butanoateHCID 229884272-[4-(Methylsulfonyl)phenyl]-1-ethanol

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(4-hydroxybenzyl)butanoate (0.50 g; 2.5 mmole) and 2-[4-(methylsulfonyl)phenyl]ethanol (0.52 g, 2.5 mmole) were mixed in dichloromethane (10 ml). ADDP (0.76 g, 3.0 mmole) was added followed by addition of triphenylphosphine ((0.79 g, 3.0 mmole). The reaction was interrupted after 16 hours. Triphenylphosphine oxide formed in the reaction was filtered off and the filtrate was evaporated. Chromatography of the crude material from methanol and dichloromethane, gradient eluation from 0-32% gave 0.64 g (66% yield) of the product.

Sources & evidence

ORD record
ord-8338b72c4c834992ae4b275bc0af7d9b
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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