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

HRID 1836861노트

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HRID 1836861 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 84541-Methylpyrrolidine용매

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온도
175 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8c24cb5ef7ee4b918f29f1c8d480da7e
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777418B2

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