Hydrochloric Acid → HCID 13359894, compound

HRID 1981859Notes

Reaction equation

HRID 1981859 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][P:11]([OH:13])[OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](Cl)(C)C.[C:19](#[N:22])[CH:20]=[CH2:21].Cl>C(Cl)(Cl)Cl.C(N(CC)CC)C>[OH:12][P:11]([CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH2:21][CH2:20][C:19]#[N:22])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 7855AcrylonitrileHCID 132746654-Phenylbutylphosphonous acid

Product 1

HCID 13359894HCID 13359894, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-phenylbutyl phosphonous acid (0.44 g, 0.0022 mole) in chloroform (15 ml) was added triethylamine (0.68 ml), trimethyl silylchloride (0.61 ml) and acrylonitrile (0.17 ml) and the reaction mixture was stirred at room temperature for 18 hours; the mixture was poured into crushed ice (15 gm) containing 10 ml 10% HCl acid. It was shaken in a separatory funnel; a chloroform layer was evaporated, and the aqueous layer extracted once with 20 ml chloroform. The combined organic phase was washed with water, dried over anhydrous sodium sulphate and the organic solvent removed on a rotavap to produce the title compound as a highly crystalline solid 0.5 gm (90% yield), m.p. 80°-82° C.

Workup

  1. additionthe mixture was poured
  2. stirringIt was shaken in a separatory funnel
  3. customa chloroform layer was evaporated
  4. extractionthe aqueous layer extracted once with 20 ml chloroform
  5. washThe combined organic phase was washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. customthe organic solvent removed on a rotavap

Sources & evidence

ORD record
ord-16c120c1986a4717a1de57872eb2732c
Source dataset
uspto-grants-1986_06
Patent number
US04594199

Reaction notes

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