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

HRID 1499004ノート

反応式

HRID 1499004 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23985Gold触媒HCID 63651,1-Dichloroethane溶媒2 回

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-b19218f2dab046939aa8f396b1d66b9a
出典データセット
uspto-grants-2015_12
特許番号
US09200019B2

反応ノート

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