2-(Di-tert-butylphosphino)biphenyl → HCID 90019401, compound

HRID 1499012Notes

Reaction equation

HRID 1499012 reaction equation
CC(P(C(C)(C)C)C1C(C2C=CC=CC=2)=CC=CC=1)(C)C.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[C:30][P:31](=[O:47])([O:35][C:36]([CH2:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH2:37])[O:32][CH2:33][CH3:34])=[CH:25][CH:24]=1>[Au].ClC(Cl)C>[CH2:33]([O:32][P:31]1(=[O:47])[CH:30]=[C:29]([C:26]2[CH:25]=[CH:24][C:23]([Cl:22])=[CH:28][CH:27]=2)[CH:37]=[C:36]([CH2:38][CH2:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[O:35]1)[CH3:34]

Participants

5

Reactant 2

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 76764665HCID 76764665, compound

Product 1

HCID 90019401HCID 90019401, compoundYield 72%

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, ethyl 5-phenylpent-1-en-2-yl 2-(4-chlorophenyl)ethynylphosphonate (Example 23, 116 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-p-chlorophenyl-6-3-phenylpropyl-1,2-oxaphosphorin 2-oxide (83.3 mg, 72%) 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-db2e440aeb2f4b5eb03c098df242c8f5
Source dataset
uspto-grants-2015_12
Patent number
US09200019B2

Reaction notes

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