Ammonium Hydroxide → 6-Cyano-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

HRID 1836861ノート

反応式

HRID 1836861 の反応式
[Cu][C:2]#[N:3].Br[C:5]1[C:14]([CH3:15])=[CH:13][C:12]2[C:11]([CH3:17])([CH3:16])[CH2:10][CH2:9][C:8]([CH3:19])([CH3:18])[C:7]=2[CH:6]=1.[OH-].[NH4+]>CN1CCCC1>[C:2]([C:5]1[C:14]([CH3:15])=[CH:13][C:12]2[C:11]([CH3:17])([CH3:16])[CH2:10][CH2:9][C:8]([CH3:19])([CH3:18])[C:7]=2[CH:6]=1)#[N:3]

参加物

5

反応物 3

HCID 14923Ammonium HydroxideHCID 100393466-Bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthaleneHCID 178418546HCID 178418546、化合物

生成物 1

HCID 35534396-Cyano-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene収率 98.1%

試薬・触媒・溶媒 1

HCID 84541-Methylpyrrolidine溶媒

反応条件

温度
175 °C

実験手順

28.9 g (322 mmol) of copper(I) cyanide was added to 22.7 g (80.7 mmol) of 2-bromo-3-methyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene in 270 mL of N-methyl pyrrolidine. The reaction mixture was heated at 175° C. After 16 hours, the mixture was cooled to room temperature and treated with 400 mL of 10% aqueous ammonium hydroxide. The reaction mixture was filtered to remove salts and the solids were extracted with hot ethyl acetate. The combined organic fractions were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The product was purified by gradient elution through a pad of silica gel (hexane-5% ethyl acetate/hexane) to give 18 g (95%) of 2-cyano-3-methyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (M+=227).

後処理

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationThe reaction mixture was filtered
  3. customto remove salts
  4. extractionthe solids were extracted with hot ethyl acetate
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe product was purified by gradient elution through a pad of silica gel (hexane-5% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-8c24cb5ef7ee4b918f29f1c8d480da7e
出典データセット
uspto-grants-2004_08
特許番号
US06777418B2

反応ノート

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