Tetrahydrofuran → Triphenylphosphine Oxide

HRID 1448714Notes

Reaction equation

HRID 1448714 reaction equation
C([N-]C(C)C)(C)C.[Li+].[Cl-].[CH3:10][O:11][CH2:12][P+:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[O:32]1CCCC1>C1(C)C=CC=CC=1>[CH3:10][O:11][CH:12]=[P:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:14]1([P:13](=[O:32])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 2724682Lithium diisopropylamide

Product 2

HCID 13097Triphenylphosphine OxideHCID 11748776(Methoxymethylene)triphenylphosphorane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of methoxymethylenetriphenylphosphorane is prepared by addition of lithium diisopropyl amide (10.6 g, 0.1 mole) in dry tetrahydrofuran (100 ml) to a slurry of methoxy methyl triphenyl phosphonium chloride (34.3 g, 0.1 mole) in dry toluene (400 ml) under nitrogen at 0° C. The resulting red Wittig reagent is stirred at 0° C. for 30 minutes prior to use. To this solution is added endo-5-t-butyldimethylsilyloxy-exo-3a, 4,7,7a-tetrahydro-4,7-epoxyisobenzofuran-2-ol (14.3 g, 0.05 mole) via a solids addition funnel and the resulting mixture is stirred at 25° C. for 2 hours. The mixture is acidified to pH 5 with 10hydrochloric acid and extracted with ether (three 200 ml portions). The solvents are removed under vacuum and the residue is dissolved in ether and this solution chilled yielding crystalline triphenylphosphine oxide. The filtrate is concentrated yielding the title compound which is purified by column chromatography on silica gel.

Workup

  1. additionvia a solids addition funnel
  2. extractionextracted with ether (three 200 ml portions)
  3. customThe solvents are removed under vacuum
  4. dissolutionthe residue is dissolved in ether
  5. temperaturethis solution chilled

Sources & evidence

ORD record
ord-a7b9a3b5e7c54c47ad77d60b6de9e6dd
Source dataset
uspto-grants-1980_02
Patent number
US04187236

Reaction notes

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