Cyanuric chloride → 3-[3-Chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]cyclobutanol

HRID 1499828노트

반응식

HRID 1499828 반응식
[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([CH:13]2[CH2:16][CH:15]([OH:17])[CH2:14]2)[C:5]([O:11][CH3:12])=[C:6]([CH:8](O)[CH3:9])[CH:7]=1.N1C(Cl)=NC(Cl)=NC=1[Cl:21]>CS(C)=O.CCOCC.O>[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([CH:13]2[CH2:16][CH:15]([OH:17])[CH2:14]2)[C:5]([O:11][CH3:12])=[C:6]([CH:8]([Cl:21])[CH3:9])[CH:7]=1

참가 물질

6

반응물 2

HCID 7954Cyanuric chlorideHCID 866777523-[3-Chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]cyclobutanol

생성물 1

HCID 866777513-[3-Chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]cyclobutanol수율 40.3%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

To a solution of 3-[3-chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]cyclobutanol (170 mg, 0.628 mmol) in dimethyl sulfoxide (1 mL) was added cyanuric chloride (64 mg, 0.34 mmol). After stirred overnight, the reaction mixture was diluted with ether and water. The aqueous layer was extracted with ethyl acetate once. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The crude was purified with silica gel column to give the desired product (39.6 mg, 22%). LCMS calculated for C14H18ClO2(M−Cl)+: m/z=253.1; Found: 253.2.

후처리

  1. extractionThe aqueous layer was extracted with ethyl acetate once
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified with silica gel column

출처 및 근거

ORD 기록
ord-82093d9be358456da73e43e47b49e067
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199982B2

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