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

HRID 1614923노트

반응식

HRID 1614923 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

(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.

후처리

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

출처 및 근거

ORD 기록
ord-f1e890d60c44408586cd225a88eb3883
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765722B2

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