Triphenylphosphine → Triphenylphosphine Oxide

HRID 987117Notes

Reaction equation

HRID 987117 reaction equation
C(C1C=CC(CC[OH:9])=CC=1)#N.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.[C:30]1([P:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[C:43]1([P:36](=[O:9])([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 28008154-(2-Hydroxyethyl)benzonitrile

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-ethoxy-3-(4-hydroxyphenyl) propanoate, described in example 3(b)(6.62 g; 27.78 mmole) and p-cyanophenethyl alcohol (2.73 g; 18.52 mmole) were mixed in dichloromethane (85 ml). ADDP (7.01 g; 27.78 mmole) was added followed by addition of triphenylphosphine (5.83 g; 22.23 mmole). The reaction was interrupted after 2 hours. Triphenylphosphine oxide formed in the reaction was filtered off and the filtrate was evaporated. The residue was purified bychromatography on silica gel using first dichloromethane and then petroleum ether:diethyl ether as eluants giving a mixture of product and starting material which was dissolved in ethyl acetate and washed with sodium hydroxide (1 N). The organic phase was washed with water, dried (sodium sulfate), filtered and the solvent was evaporated to give 4.23 g (yield 62%) of the desired product.

Sources & evidence

ORD record
ord-68cad41a34f74ff186f74c69f7ff7d27
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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