Diphenylphosphine → HCID 20189071, compound

HRID 1789261Notes

Reaction equation

HRID 1789261 reaction equation
[C:1]1([PH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([S:16]([CH:19]=[CH2:20])(=[O:18])=[O:17])[CH3:15]>>[CH2:14]([S:16]([CH2:19][CH2:20][P:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)(=[O:18])=[O:17])[CH3:15]

Participants

3

Reactant 2

HCID 70017DiphenylphosphineHCID 74680(Ethylsulfonyl)ethene

Product 1

HCID 20189071HCID 20189071, compoundYield 69%

Procedure

A mixture of 64 g (0.34 mole) of diphenyl phosphine and 40.2 g (0.33 mole) of highly reactive, freshly distilled vinyl ethyl sulfone monomer was irradiated in the usual manner. To suppress polymer forming side reactions the temperature of the reaction mixture was kept below 5° C. by an ice-water bath and the u.v. irradiation was limited to 105 minutes. The adduct formed crystallized from the liquid mixture by the end of the reaction period. Consequently, the reaction mixture was filtered with suction to recover the crude, crystalline product, i.e. 2-ethylsulfonylethyl diphenyl phosphine. The crude, dried product (94 g, 94%) was recrystallized from 670 ml methanol to yield 69 g (69%) of the compound (of unpleasant odor) as a white crystalline solid (Table 4).

Workup

  1. customwas irradiated in the usual manner
  2. customTo suppress polymer forming side reactions the temperature of the reaction mixture
  3. customwas kept below 5° C. by an ice-water bath
  4. customirradiation
  5. customThe adduct formed
  6. customcrystallized from the liquid mixture by the end of the reaction period
  7. filtrationConsequently, the reaction mixture was filtered with suction
  8. customto recover the crude, crystalline product, i.e. 2-ethylsulfonylethyl diphenyl phosphine
  9. customThe crude, dried product (94 g, 94%) was recrystallized from 670 ml methanol

Sources & evidence

ORD record
ord-1228ed91a2884b5bbc8e0d36a8f7735b
Source dataset
uspto-grants-1987_08
Patent number
US04687866

Reaction notes

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