1,1-Dichloroethane → HCID 90019178, compound

HRID 1498999Notes

Reaction equation

HRID 1498999 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:50])([O:38][C:39]([CH2:41][CH2:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=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:50])[CH:33]=[C:32]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:40]=[C:39]([CH2:41][CH2:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[O:38]1)[CH3:37]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 76764666HCID 76764666, compound

Product 1

HCID 90019178HCID 90019178, compoundYield 84%

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 5-phenylpent-1-en-2-yl phenylethynylphosphonate (Example 5, 106.3 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-6-3-phenylpropyl-1,2-oxaphosphorin 2-oxide (89.3 mg, 84%) 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-efeb370be45d49b4a7b3e70f9cf12e87
Source dataset
uspto-grants-2015_12
Patent number
US09200019B2

Reaction notes

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