(Prop-2-yn-1-yl)cyclohexane → 2-Ethoxy-4-p-tolyl-6-(cyclohexylmethyl)-1,2-oxaphosphorin 2-oxide

HRID 1499004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1499004
CC(P(C(C)(C)C)[C:6]1[C:11]([C:12]2C=CC=[CH:14][CH:13]=2)=[CH:10][CH:9]=[CH:8][CH:7]=1)(C)C.[C:22]1([CH3:36])[CH:27]=[CH:26][C:25]([C:28]#[C:29][P:30](=[O:35])([OH:34])[O:31][CH2:32][CH3:33])=[CH:24][CH:23]=1.C(C1CCCCC1)C#C>[Au].ClC(Cl)C>[CH2:32]([O:31][P:30]1(=[O:34])[CH:29]=[C:28]([C:25]2[CH:24]=[CH:23][C:22]([CH3:36])=[CH:27][CH:26]=2)[CH:14]=[C:13]([CH2:12][CH:11]2[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)[O:35]1)[CH3:33]

Komponenten

6

Edukt 3

HCID 87265(Prop-2-yn-1-yl)cyclohexaneHCID 27342152-(Di-tert-butylphosphino)biphenyl2×HCID 71546601Ethyl hydrogen p-tolylethynylphosphonate

Produkt 1

HCID 900192492-Ethoxy-4-p-tolyl-6-(cyclohexylmethyl)-1,2-oxaphosphorin 2-oxideAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23985GoldKatalysatorHCID 63651,1-DichloroethaneLösungsmittel2×

Versuchsvorschrift

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 p-tolylethynylphosphonate (67.3 mg, 0.3 mmol) diluted with 0.5 mL of dichloroethane was added thereto, and finally, prop-2-ynylcyclohexane (73.2 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-tolyl-6-(cyclohexylmethyl)-1,2-oxaphosphorin 2-oxide (66.5 mg, 64%) which is a title compound.

Aufarbeitung

  1. additionwas added
  2. customAfter the solvent was removed under low atmospheric pressure
  3. customthe product was separated by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b19218f2dab046939aa8f396b1d66b9a
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09200019B2

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