Propargyl alcohol → 3-(3,4-Dichlorophenyl)-2-propynal

HRID 1096710

反応式

HRID 1096710 の反応式
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Cl:12][C:13]1[CH:14]=[C:15]([C:20]#[C:21][CH2:22][OH:23])[CH:16]=[CH:17][C:18]=1[Cl:19].CCCCCCC.C(OCC)(=O)C.C(O)C#C>ClCCl>[Cl:12][C:13]1[CH:14]=[C:15]([C:20]#[C:21][CH:22]=[O:23])[CH:16]=[CH:17][C:18]=1[Cl:19]

参加物

6

反応物 4

HCID 7859Propargyl alcoholHCID 21899848Ethylacetate heptaneHCID 230063813-(3,4-Dichlorophenyl)prop-2-yn-1-olHCID 178418287HCID 178418287、化合物

生成物 1

HCID 592560003-(3,4-Dichlorophenyl)-2-propynal収率 49%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Pyridinium chlorochromate (24.23 g; 112.4 mmol; 2 eq) was added to a stirred solution of 3-(3,4-dichlorophenyl)prop-2-yn-1-ol (11.3 g; 56.2 mmol) in dichloromethane (225 mL) at room temperature. The mixture was stirred for 3.5 h until TLC (2:1 heptane/ethyl acetate) indicated the disappearance of the starting propargyl alcohol. The mixture was then filtered through a bed of celite, and the filter cake was rinsed with dichloromethane (150 mL). The dichloromethane was concentrated using a rotary evaporator to give the desired product (5.48 g; 27.5 mmol; 49%) which was used in the next step without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.20 (d, 1H) 7.31 (d, 1H) 7.51 (s, 1H) 9.43 (s, 1H).

後処理

  1. filtrationThe mixture was then filtered through a bed of celite
  2. washthe filter cake was rinsed with dichloromethane (150 mL)
  3. concentrationThe dichloromethane was concentrated
  4. customa rotary evaporator

出典と根拠

ORDレコード
ord-05ccef29ddc74362bb60f7d9c91d3186
出典データセット
uspto-grants-2012_03
特許番号
US08138377B2

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