p-Ethynyltoluene → HCID 72705808, compound

HRID 1498993Notes

Reaction equation

HRID 1498993 reaction equation
CC(P(C(C)(C)C)C1C(C2C=CC=CC=2)=CC=CC=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:36]([C:38]1[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=1)#[CH:37]>[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:37]=[C:36]([C:38]2[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=2)[O:35]1)[CH3:33]

Participants

6

Reactant 3

HCID 13018p-EthynyltolueneHCID 27342152-(Di-tert-butylphosphino)biphenyl2×HCID 86041878HCID 86041878, compound

Product 1

HCID 72705808HCID 72705808, compoundYield 34%

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-ethynyl-4-methylbenzene (174 mg, 1.5 mmol) was put thereinto, followed by stirring at 30° C. for 16 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-p-methylphenyl-1,2-oxaphosphorin 2-oxide (33.2 mg, 34%) which is a title compound.

Workup

  1. additionwas added
  2. additionwas added
  3. stirringby stirring at 30° C. for 16 hours
  4. customAfter the solvent was removed under low atmospheric pressure
  5. customthe product was separated by chromatography

Sources & evidence

ORD record
ord-2f7bb2fb4ab7473fb544d00367162b7d
Source dataset
uspto-grants-2015_12
Patent number
US09200019B2

Reaction notes

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