Dimethylformamide → 6-Bromo-1,2,3,4-tetrahydro-7-methoxy-1,1,4,4-tetramethylnaphthalene

HRID 1057971ノート

反応式

HRID 1057971 の反応式
[Br:1][C:2]1[C:3]([OH:16])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[CH3:17]N(C=O)C.[H-].[Na+].IC>O>[Br:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 107793113-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

生成物 1

HCID 107327466-Bromo-1,2,3,4-tetrahydro-7-methoxy-1,1,4,4-tetramethylnaphthalene

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

7 g (24.7 mmol) of 3-bromo-2-hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene and 40 ml of DMF are introduced into a three-necked flask under a stream of nitrogen. 890 mg (29.6 mmol) of sodium hydride (80% in oil) are added portionwise and the mixture is stirred until the evolution of gas has ceased. 1.7 ml (27 mmol) of iodomethane are then added and the mixture is stirred at room temperature for one hour. The reaction medium is poured into water and extracted with ethyl ether, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. 7.3 g (99%) of the expected product are collected in the form of an oil which crystallizes slowly. Melting point 77-8° C.

後処理

  1. stirringthe mixture is stirred at room temperature for one hour
  2. extractionextracted with ethyl ether
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. custom7.3 g (99%) of the expected product are collected in the form of an oil which
  7. customcrystallizes slowly

出典と根拠

ORDレコード
ord-fe8b008f440f4d0c8df10b7d7027a719
出典データセット
uspto-grants-2003_02
特許番号
US06515021B1

反応ノート

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