Triphenylphosphine → HCID 19605229, compound

HRID 1756427Notes

Reaction equation

HRID 1756427 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.O[CH2:35][C:36]1[CH:47]=[CH:46][C:39]([C:40]([O:42][CH2:43][CH:44]=[CH2:45])=[O:41])=[CH:38][CH:37]=1.[C:48]([OH:51])(=[S:50])[CH3:49]>C1COCC1.O>[C:48]([S:50][CH2:35][C:36]1[CH:47]=[CH:46][C:39]([C:40]([O:42][CH2:43][CH:44]=[CH2:45])=[O:41])=[CH:38][CH:37]=1)(=[O:51])[CH3:49]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 22392687Allyl 4-hydroxymethylbenzoateHCID 178418634HCID 178418634, compound

Product 1

HCID 19605229HCID 19605229, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

25.7 g (98 mmol) of triphenylphosphine and 100 ml of THF are introduced into a round-bottomed flask and 19.8 g (98 mmol) of diisopropyl azodicarboxylate, dissolved in 150 ml of THF, are added dropwise at 0° C. The mixture is stirred for one hour at 0° C. and a mixture of 9.4 g (49 mmol) of allyl 4-hydroxymethylbenzoate and 7 ml (98 mmol) of thioacetic acid is then added. The mixture is stirred at room temperature for four hours, the reaction medium is poured into water, the mixture is extracted with ethyl ether and the organic phase is separated after settling has taken place, then dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column and eluted with a mixture of dichloromethane and hexane (60:40). 12.2 g (100%) of the expected product are obtained in the form of an oil.

Workup

  1. additionare added dropwise at 0° C
  2. additionis then added
  3. stirringThe mixture is stirred at room temperature for four hours
  4. extractionthe mixture is extracted with ethyl ether
  5. customthe organic phase is separated after settling
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue obtained
  9. customis purified by chromatography on a silica column
  10. washeluted with a mixture of dichloromethane and hexane (60:40)

Sources & evidence

ORD record
ord-0f7e628a7a24435f8edf5e02837a63b4
Source dataset
uspto-grants-1995_08
Patent number
US05439925

Reaction notes

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