Phenylacetylene → HCID 10386365, compound

HRID 36169Notes

Reaction equation

HRID 36169 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:19]([O:21][P:22]([C:27]([P:29](=[O:36])([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])=[CH2:28])(=[O:26])[O:23][CH2:24][CH3:25])[CH3:20]>C1COCC1>[CH2:31]([O:30][P:29]([CH:27]([P:22](=[O:26])([O:21][CH2:19][CH3:20])[O:23][CH2:24][CH3:25])[CH2:28][C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:36])[O:33][CH2:34][CH3:35])[CH3:32]

Participants

5

Reactant 3

HCID 10821PhenylacetyleneHCID 2733832Lithium HexamethyldisilazideHCID 11022954Tetraethyl vinylidene phosphonate

Product 1

HCID 10386365HCID 10386365, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Phenylacetylene (IX, 4.4 g) is dissolved in THF (43 ml), cooled to -78°, and treated with lithium hexamethyldisilazide (1M in THF, 43 ml). The reaction is stirred for 30 min, then a solution of ethenylidenebisphosphonic acid tetraethyl ester (10.7 g) in THF (36 ml) is added and the reaction warmed to 22° for 1 hour. The reaction is quenched with water, extracted thrice with ethyl acetate. The organics were then washed with water, hydrochloric acid (10%), saturated sodium bicarbonate, and saline, dried with magnesium sulfate, and concentrated. The concentrate is purified by distillation, bp 0.1 195°-200°.

Workup

  1. temperaturecooled to -78°
  2. temperaturethe reaction warmed to 22° for 1 hour
  3. customThe reaction is quenched with water
  4. extractionextracted thrice with ethyl acetate
  5. washThe organics were then washed with water, hydrochloric acid (10%), saturated sodium bicarbonate, and saline
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated
  8. distillationThe concentrate is purified by distillation, bp 0.1 195°-200°

Sources & evidence

ORD record
ord-5a2142a218f341599ecf6dcf7e346059
Source dataset
uspto-grants-1995_05
Patent number
US05412141

Reaction notes

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