Triphenylphosphine → HCID 178459887, compound

HRID 2279435Notes

Reaction equation

[N:1]([C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])=[N:2][C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4].[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH:31]1[CH:30]=[CH:29][C:28]([P:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:33][CH:32]=1.[CH3:8][CH:6]([O:5][C:3](/[N:2]=[N:1]/[C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])=[O:4])[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Diisopropyl azodicarboxylate (DIAD, 1 eq) is added dropwise to a well-stirred solution of triphenylphosphine (1 eq) in THF (0.4 M) at 0° C. under nitrogen. After completion of the addition, the mixture is stirred at 0° C. for an additional 30 min. The white solid obtained is collected by filtration (use medium sized fitted filters) and washed with cold anhydrous THF until the washes are colorless. Finally, the white precipitate is washed once with anhydrous Et2O. The adduct is then dried well in vacuo, and stored under nitrogen. (It is important to store this reagent under anhydrous conditions!) The adduct can be used in place of the separately added reagents in Mitsunobu-type reactions.

Workup

additionAfter completion of the addition
customThe white solid obtained
filtrationis collected by filtration (use medium sized fitted filters)
washwashed with cold anhydrous THF until the washes
washFinally, the white precipitate is washed once with anhydrous Et2O
customThe adduct is then dried well in vacuo

Sources & evidence

ORD record: ord-97728d3f4ad54ec284e2d9767842d1ec
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133235B2

Reaction notes

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