Triethylamine → Ethyl 5-chloropent-1-en-2-yl p-tolylethynylphosphonate

HRID 1499001Notes

Reaction equation

HRID 1499001 reaction equation
CC(P(C(C)(C)C)C1C(C2C=CC=CC=2)=CC=CC=1)(C)C.C(N(CC)CC)C.[C:29]1([CH3:43])[CH:34]=[CH:33][C:32]([C:35]#[C:36][P:37](=[O:42])([OH:41])[O:38][CH2:39][CH3:40])=[CH:31][CH:30]=1.[Cl:44][CH2:45][CH2:46][CH2:47][C:48]#[CH:49]>[Au].ClC(Cl)C>[C:29]1([CH3:43])[CH:30]=[CH:31][C:32]([C:35]#[C:36][P:37](=[O:41])([O:42][C:48]([CH2:47][CH2:46][CH2:45][Cl:44])=[CH2:49])[O:38][CH2:39][CH3:40])=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 843081-Pentyne, 5-chloro-HCID 27342152-(Di-tert-butylphosphino)biphenyl2×HCID 71546601Ethyl hydrogen p-tolylethynylphosphonate

Product 1

HCID 90019180Ethyl 5-chloropent-1-en-2-yl p-tolylethynylphosphonateYield 70%

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) and triethylamine (Et3N) (3.0 mg, 0.03 mmol) were put into a reaction container, and dichloroethane (0.4 mL) was put thereinto. After stirring at room temperature for 5 minutes, ethyl hydrogen p-tolylethynylphosphonate (67.3 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 ethyl 5-chloropent-1-en-2-yl p-tolylethynylphosphonate (68.5 mg, 70%) 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-14c9c66d7c7a49eb944b9d8da3dfddeb
Source dataset
uspto-grants-2015_12
Patent number
US09200019B2

Reaction notes

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