1-Pentyne, 5-chloro- → HCID 90019362, compound

HRID 1499007Notes

Reaction equation

HRID 1499007 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].[Cl:34][CH2:35][CH2:36][CH2:37][C:38]#[CH:39]>[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:39]=[C:38]([CH2:37][CH2:36][CH2:35][Cl:34])[O:33]1)[CH3:31]

Participants

6

Reactant 3

HCID 843081-Pentyne, 5-chloro-HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 90020040HCID 90020040, compound

Product 1

HCID 90019362HCID 90019362, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23985GoldCatalystHCID 63651,1-DichloroethaneSolvent2×

Procedure

Method 2—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 hydrogen hex-1-ynylphosphonate (57.0 mg, 0.3 mmol) diluted with 0.5 mL of dichloroethane was added thereto, and finally, 5-chloropent-1-yne (61.5 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-chlorpropyl-1,2-oxaphosphorin 2-oxide (56.1 mg, 64%) 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-36908bfedc424c28990294c154cae7b5
Source dataset
uspto-grants-2015_12
Patent number
US09200019B2

Reaction notes

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