Piconol → Triphenylphosphine Oxide

HRID 856968Notes

Reaction equation

HRID 856968 reaction equation
[OH:1]C1C=C(C=CC=1)C(N(OC)C)=O.[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1CO.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:27]1([P:20](=[O:1])([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 11474PiconolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 218653763-hydroxy-N-methoxy-N-methylbenzamide

Product 1

HCID 13097Triphenylphosphine OxideYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.21 g (10.0 mmol) B2, 2.89 g (11.0 mmol) triphenylphosphine and 1.20 g (11.0 mmol) pyridine-2-methanol in 30 ml dry tetrahydrofuran a solution of 1.92 g (11.0 mmol) diethyl azodicarboxylate in 5 ml dry tetrahydrofuran was added and the mixture was stirred at room temperature for 2 hours. After removal of the solvent and column chromatography on Silica (hexane/ethyl acetate 2:1) 2.81 g B3 were obtained as a light yellow oil (72% yield assuming 30 mol % impurity of triphenylphosphine oxide (measured by NMR)). Due to the problems with the separation of the impurities in this particular example the experiment was repeated with PS-bound triphenylphosphine to give pure B3 in 58% yield.

Workup

  1. customAfter removal of the solvent and column chromatography on Silica (hexane/ethyl acetate 2:1) 2.81 g B3

Sources & evidence

ORD record
ord-85438038cd914b269681cedeae48b90d
Source dataset
uspto-grants-2006_12
Patent number
US07144889B2

Reaction notes

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