2-Bromopropane → 5-Isopropoxy-6-methoxy-1,2,3,4-tetrahydronaphtalene

HRID 33948

反応式

HRID 33948 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4]=1[OH:13].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:21]([CH3:23])[CH3:22]>CC(C)=O>[CH:21]([O:13][C:4]1[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][CH2:9]2)([CH3:23])[CH3:22]

参加物

5

反応物 3

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 574358992-Methoxy-5,6,7,8-tetrahydronaphthalen-1-ol

生成物 1

HCID 574359005-Isopropoxy-6-methoxy-1,2,3,4-tetrahydronaphtalene収率 93%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

33 (4.55 g, 25.5 mmol) was charged in a 250 mL round bottom flask, equipped with a reflux condenser, under nitrogen gas. 50 mL of anhydrous acetone was added followed by cesium carbonate (66.55 g, 204.3 mmol). 2-bromopropane (23.94 mL, 255.0 mmol) was added and the reaction mixture was refluxed for 12 h. The solvent was filtered and evaporated in vacuo and purified by flash column chromatography (slilica gel, 1:99 EtOAc:Hexanes) to afford 5.2 g (93%) of 5-isopropoxy-6-methoxy-1,2,3,4-tetrahydronaphtalene (34). Rf value: 0.615 (15:85 EtOAc:Hexanes).

後処理

  1. customequipped with a reflux condenser, under nitrogen gas
  2. temperaturethe reaction mixture was refluxed for 12 h
  3. filtrationThe solvent was filtered
  4. customevaporated in vacuo
  5. custompurified by flash column chromatography (slilica gel, 1:99 EtOAc:Hexanes)

出典と根拠

ORDレコード
ord-7d06dbbb8e7b4673802ee94161a74626
出典データセット
uspto-grants-2008_09
特許番号
US07429681B2

関連ノート

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