Sodium Hydroxide → 5,6,11,12-Tetrahydrodibenzo[b,f]azocine

HRID 477442

반응식

HRID 477442 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1[C:18]2[CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[C:13](=O)[NH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].[H][H]>C1COCC1>[CH:7]1[C:18]2[CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[CH2:13][NH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 801465,6,11,12-Tetrahydrodibenz[b,f]azocin-6-oneHCID 21226445Aluminium lithium hydrideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 6105775,6,11,12-Tetrahydrodibenzo[b,f]azocine수율 98.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

In a two liter three neck round bottom flask (argon atmosphere) was placed 300 ml of dry THF and 30.06 g (0.8 mole) of LAH was added cautiously. The reaction mixture was stirred and a suspension of 89.31 g (0.4 mole) of 11,12-dihydrodibenz[b,f]azocin-6(5H)-one (Aldrich) in 400 ml of hot THF was added dropwise. After the addition, the reaction mixture was stirred and heated to reflux for 8.5 hr. The reaction mixture was cooled to RT and 60 ml of 1N sodium hydroxide was added with caution (hydrogen evolution). The reaction mixture was stirred and heated to reflux for 0.5 hr to give a white suspension. The solid was removed by filtration and washed with several portions of warm THF. The filtrate was concentrated to dryness in vacuo to give 82.5 g of white solid title compound of 99.5% purity by g.c. The product was used in the next step without further purification.

후처리

  1. additionwas added cautiously
  2. additionwas added dropwise
  3. additionAfter the addition
  4. stirringthe reaction mixture was stirred
  5. temperatureheated
  6. temperatureto reflux for 8.5 hr
  7. stirringThe reaction mixture was stirred
  8. temperatureheated
  9. temperatureto reflux for 0.5 hr
  10. customto give a white suspension
  11. customThe solid was removed by filtration
  12. washwashed with several portions of warm THF
  13. concentrationThe filtrate was concentrated to dryness in vacuo

출처 및 근거

ORD 기록
ord-5e4aad555554431386f8d0720ef83a73
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04888335

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