1,1-Dichloroethane → HCID 90019824, compound

HRID 1498996Notes

Reaction equation

HRID 1498996 reaction equation
CC(P(C(C)(C)C)C1C(C2C=CC=CC=2)=CC=CC=1)(C)C.ClC(Cl)C.[C:26]1([C:32]#[C:33][P:34](=[O:48])([O:38][C:39]([CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH2:40])[O:35][CH2:36][CH3:37])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>[Au]>[CH2:36]([O:35][P:34]1(=[O:48])[CH:33]=[C:32]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:40]=[C:39]([CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[O:38]1)[CH3:37]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 90019511HCID 90019511, compound

Product 1

HCID 90019824HCID 90019824, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 23985GoldCatalyst

Procedure

Method 1—A gold (Ag(I)) catalyst {[Au(JohnPhos)NCCH3]+SbF6—} [JohnPhos:(2-biphenyl)di-tent-butylphosphine] (11.3 mg, 0.015 mmol) was put into a reaction container, and dichloroethane (0.4 mL) was put thereinto. After stirring at room temperature for 5 minutes, ethyl 3-phenylprop-1en-2-yl phenylethynylphosphonate (example 3, 98 mg, 0.3 mmol) was put thereinto, and when all of the starting materials disappeared in the TLC, the reaction was allowed to be completed. After the solvent was removed under low atmospheric pressure, the product was separated by chromatography to obtain 2-ethoxy-4-phenyl-6-benzyl-1,2-oxaphosphorin 2-oxide (84.1 mg, 86%) which is a title compound.

Workup

  1. customAfter the solvent was removed under low atmospheric pressure
  2. customthe product was separated by chromatography

Sources & evidence

ORD record
ord-4c5de263287d43ab83e7b63a8f94b48c
Source dataset
uspto-grants-2015_12
Patent number
US09200019B2

Reaction notes

Loading…