2-(Di-tert-butylphosphino)biphenyl → HCID 90019362, compound

HRID 1499006Notes

Reaction equation

HRID 1499006 reaction equation
[CH3:1][C:2](P(C(C)(C)C)C1C(C2C=CC=CC=2)=CC=CC=1)(C)C.C([CH:24]([CH2:37][CH2:38][CH3:39])[C:25]#[C:26][P:27](=[O:36])([O-:35])[O:28][C:29]([CH2:31][CH2:32][CH2:33][Cl:34])=[CH2:30])C>[Au].ClC(Cl)C>[CH2:1]([O:35][P:27]1(=[O:36])[CH:26]=[C:25]([CH2:24][CH2:37][CH2:38][CH3:39])[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][Cl:34])[O:28]1)[CH3:2]

Participants

5

Reactant 2

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 131734236HCID 131734236, compound

Product 1

HCID 90019362HCID 90019362, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23985GoldCatalystHCID 63651,1-DichloroethaneSolvent2×

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, 5-chloropent-1-en-2yl ethylhex-1-ynylphosphonate (Example 17, 87.6 mg, 0.3 mmol) diluted with 0.5 mL of dichloroethane was added thereto, 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-n-butyl-6-3-chlorpropyl-1,2-oxaphosphorin 2-oxide (82.3 mg, 94%) which is a title compound.

Workup

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

Sources & evidence

ORD record
ord-1d932529ba8c4e7a92716fee71351e11
Source dataset
uspto-grants-2015_12
Patent number
US09200019B2

Reaction notes

Loading…