Methyl iodide → 4-Benzyloxy-2-methoxy-1-methylsulfanyl-benzene

HRID 732757ノート

反応式

HRID 732757 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([SH:16])=[C:13](O)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O-:20])([O-])=O.[K+].[K+].[CH3:23]I>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([S:16][CH3:23])=[C:13]([O:20][CH3:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 219047055-(Benzyloxy)-2-sulfanylphenol

生成物 1

HCID 219046734-Benzyloxy-2-methoxy-1-methylsulfanyl-benzene収率 68%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Dissolve 5-benzyloxy-2-mercapto-phenol (17.8 g, 76.72 mmol) in DMF (300 mL) and add K2CO3 (31.8 g, 0.23 mol) and MeI (32.7 g, 0.23 mol). Stir the reaction mixture at room temperature overnight. Add water (800 mL) and extract the aqueous layer with EtOAc (3×800 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica, 5-20% of EtOAc/hexane) to give 13.5 g of 4-benzyloxy-2-methoxy-1-methylsulfanyl-benzene (68%).

後処理

  1. extractionAdd water (800 mL) and extract the aqueous layer with EtOAc (3×800 mL)
  2. dry with materialCombine the organic layers and dry with Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify by flash column chromatography (silica, 5-20% of EtOAc/hexane)

出典と根拠

ORDレコード
ord-f55f68ab57754b79b61ce6bde7cb7bf9
出典データセット
uspto-grants-2009_09
特許番号
US07585977B2

反応ノート

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