5-Phenyl-1-pentyne → HCID 118208393, compound

HRID 1499009Notes

Reaction equation

HRID 1499009 reaction equation
CC(P(C(C)(C)C)C1C(C2C=CC=CC=2)=CC=CC=1)(C)C.[C:22]([P:28](=[O:33])([OH:32])[O:29][CH2:30][CH3:31])#[C:23][CH2:24][CH2:25][CH2:26][CH3:27].[CH2:34]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:35][CH2:36][C:37]#[CH:38]>[Au].ClC(Cl)C>[CH2:30]([O:29][P:28]1(=[O:32])[CH:22]=[C:23]([CH2:24][CH2:25][CH2:26][CH3:27])[CH:38]=[C:37]([CH2:36][CH2:35][CH2:34][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[O:33]1)[CH3:31]

Participants

6

Reactant 3

HCID 745735-Phenyl-1-pentyneHCID 27342152-(Di-tert-butylphosphino)biphenyl2×HCID 90020040HCID 90020040, compound

Product 1

HCID 118208393HCID 118208393, compoundYield 67%

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 put thereinto. After stirring at room temperature for 5 minutes, ethyl hydrogen hex-1-ynylphosphonate (57.0 mg, 0.3 mmol) diluted with 0.5 mL of dichloroethane was added thereto, and finally, pent-4-ynylbenzene (86.5 mg, 0.6 mmol) was put thereinto. Then, 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-phenylpropyl-1,2-oxaphosphorin 2-oxide (67.1 mg, 67%) 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-1d1d7aa026fc4de4818cf122c19a2557
Source dataset
uspto-grants-2015_12
Patent number
US09200019B2

Reaction notes

Loading…