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

HRID 1499828ノート

反応式

HRID 1499828 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-82093d9be358456da73e43e47b49e067
出典データセット
uspto-grants-2015_12
特許番号
US09199982B2

反応ノート

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