1-Pentyne, 5-chloro- → HCID 90019428, compound

HRID 1499010Notes

Reaction equation

HRID 1499010 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:36])([OH:35])[O:32][CH2:33][CH3:34])=[CH:25][CH:24]=1.[Cl:37][CH2:38][CH2:39][CH2:40][C:41]#[CH:42]>[Au].ClC(Cl)C>[CH2:33]([O:32][P:31]1(=[O:35])[CH:30]=[C:29]([C:26]2[CH:25]=[CH:24][C:23]([Cl:22])=[CH:28][CH:27]=2)[CH:42]=[C:41]([CH2:40][CH2:39][CH2:38][Cl:37])[O:36]1)[CH3:34]

Participants

6

Reactant 3

HCID 843081-Pentyne, 5-chloro-HCID 27342152-(Di-tert-butylphosphino)biphenyl2×HCID 76764661HCID 76764661, compound

Product 1

HCID 90019428HCID 90019428, compoundYield 49%

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 (4-chlorophenyl)ethynylphosphonate (73.4 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-p-chlorophenyl-6-(3-chloropropyl)-1,2-oxaphosphorin 2-oxide (51.0 mg, 49%) 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-6aaa4605ce774f168482ecb4251ac4c1
Source dataset
uspto-grants-2015_12
Patent number
US09200019B2

Reaction notes

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