Diethyl Ether → HCID 88797770, compound

HRID 1447539Notes

Reaction equation

HRID 1447539 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][CH:5]1[O:17][CH2:16][CH2:15][O:14][CH:6]1[CH2:7][CH:8]1[O:13][CH2:12][CH2:11][O:10][CH2:9]1.[C:18]1([P:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCOCC>C1C=CC=CC=1>[I-:1].[CH2:15]1[CH2:16][O:17][CH:7]([CH:8]2[O:13][CH2:12][CH2:11][O:10][CH2:9]2)[CH:6]([CH2:5][CH2:4][CH2:3][CH2:2][P+:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[O:14]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 70609554HCID 70609554, compound

Product 1

HCID 88797770HCID 88797770, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The iodide from Example XX (8.2 g, 0.023 mol) and triphenylphosphine (10 g, 0.038 mol) were dissolved in benzene (70 ml). The solution was boiled with stirring for 16 hours. After cooling, the benzene layer was decanted and the viscous residue was dissolved in a little acetone. Addition of ether gave 5.01 g (35% by weight yield) of a crystalline product, melting point 102°-104° C., while dilution of the mother liquor with ether gave a further 6.0 g (42% by weight yield) of less pure product (oil).

Workup

  1. temperatureAfter cooling
  2. customthe benzene layer was decanted
  3. dissolutionthe viscous residue was dissolved in a little acetone
  4. additionAddition of ether
  5. customgave
  6. custom5.01 g (35% by weight yield) of a crystalline product, melting point 102°-104° C.
  7. customa further 6.0 g (42% by weight yield) of less pure product (oil)

Sources & evidence

ORD record
ord-0cbb2d7f14b74cd799b2ed9d7882eadb
Source dataset
uspto-grants-1979_12
Patent number
US04177197

Reaction notes

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