Toluene → (1S)-4-Methylcyclohex-3-ene-1-carbonyl chloride

HRID 1046458ノート

反応式

HRID 1046458 の反応式
[CH3:1][C:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=O)[CH2:4][CH:3]=1.C1(C)C=CC=CC=1.C(Cl)(=O)C([Cl:21])=O>ClCCl.CN(C)C=O>[CH3:1][C:2]1[CH2:7][CH2:6][C@H:5]([C:8]([Cl:21])=[O:10])[CH2:4][CH:3]=1

参加物

6

反応物 3

HCID 1140TolueneHCID 65578Oxalyl chlorideHCID 10877190(1S)-4-methylcyclohex-3-ene-1-carboxylic acid

生成物 1

HCID 12951476(1S)-4-Methylcyclohex-3-ene-1-carbonyl chloride

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

(1S)-4-Methyl-cyclohex-3-ene-1-carboxylic acid (250 mg, 1.78 mmol), azeotropically dried by evaporation from toluene was dissolved in dichloromethane (4 mL) and treated with dimethylformamide (1 drop). The reaction mixture was cooled to 0° C. and treated dropwise with oxalyl chloride (0.42 mL, 4.5 mmol). The reaction mixture was allowed to warm to ambient temperature while stirring for 4 h. The solution was concentrated, treated with hexanes and concentrated again to afford (1S)-4-methyl-cyclohex-3-ene-1-carboxylic acid chloride as a light yellow oil which was used immediately in the next step.

後処理

  1. temperatureto warm to ambient temperature
  2. concentrationThe solution was concentrated
  3. additiontreated with hexanes
  4. concentrationconcentrated again

出典と根拠

ORDレコード
ord-256b9ca85b724328bc5042cf4249a0e8
出典データセット
uspto-grants-2013_10
特許番号
US08569302B2

反応ノート

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