1-Ethynylcyclohexene → HCID 90019777, compound

HRID 1498994Notes

Reaction equation

HRID 1498994 reaction equation
CC(P(C(C)(C)C)[C:6]1[C:11]([C:12]2C=CC=C[CH:13]=2)=[CH:10][CH:9]=[CH:8][CH:7]=1)(C)C.[C:22]1([C:28]#[C:29][P:30](=[O:35])([OH:34])[O:31][CH2:32][CH3:33])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(C1CCCCC=1)#C>[Au].ClC(Cl)C>[CH2:32]([O:31][P:30]1(=[O:34])[CH:29]=[C:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:13]=[C:12]([C:11]2[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=2)[O:35]1)[CH3:33]

Participants

6

Reactant 3

HCID 791281-EthynylcyclohexeneHCID 27342152-(Di-tert-butylphosphino)biphenyl2×HCID 86041878HCID 86041878, compound

Product 1

HCID 90019777HCID 90019777, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23985GoldCatalystHCID 63651,1-DichloroethaneSolvent2×

Procedure

A gold (Ag(I)) catalyst {[Au(JohnPhos)NCCH3]+SbF6—} [JohnPhos:(2-biphenyl)di-tert-butylphosphine] (11.3 mg, 0.015 mmol) was put into a reaction container, and dichloroethane (0.4 mL) was added thereto. After stirring at room temperature for 5 minutes, ethyl hydrogen phenylethynylphosphonate (63.0 mg, 0.3 mmol) diluted with 0.5 mL of dichloroethane was added thereto. Then 1-ethynylcyclohex-1-ene (63.6 mg, 0.6 mmol) was put thereinto, followed by stirring at 30° C. for 18 hours, 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-6-1-cyclohexenyl-1,2-oxaphosphorin 2-oxide (58.8 mg, 62%) which is a title compound.

Workup

  1. additionwas added
  2. additionwas added
  3. stirringby stirring at 30° C. for 18 hours
  4. customAfter the solvent was removed under low atmospheric pressure
  5. customthe product was separated by chromatography

Sources & evidence

ORD record
ord-395964c0de6a4f3e930a9473c595df8e
Source dataset
uspto-grants-2015_12
Patent number
US09200019B2

Reaction notes

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