1-Butanol → Agn-190205

HRID 893740노트

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HRID 893740 반응식
[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3C=CC(C#N)=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[OH-:25].[K+].[CH2:27]([OH:31])[CH2:28][CH2:29][CH3:30]>O>[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][C:28]([C:27]([OH:25])=[O:31])=[CH:29][CH:30]=3)[CH:5]=[CH:4][C:3]1=2

참가 물질

5

반응물 3

HCID 2631-ButanolHCID 14797Potassium HydroxideHCID 136048264-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzonitrile

생성물 1

HCID 10314719Agn-190205수율 44%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

2.6 g (8 millimoles) of 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-ethynyl]-benzonitrile (Example 1) and 4.6 g of 85% strength potassium hydroxide in 17 ml of n-butanol were refluxed for 1.5 hours. The cooled reaction mixture was dissolved in 100 ml of water and the solution was extracted three times with ether. The aqueous phase was freed from residual ether under reduced pressure and acidified with 2N HCL. The precipitate which had separated out was filtered off under suction, washed with water and dried in a stream of nitrogen. 2.1 g of crude product remained. Recrystallization from isopropanol gave 1.2 g (44%) of the title compound of melting point 252°-256° C., which had a purity of 99.9% according to HPLC (C18 reversed phase; 9:1 acetonitrile/H2O+0.1% of acetic acid; 100 ml/min; tR : 7 min).

후처리

  1. customThe cooled reaction mixture
  2. extractionthe solution was extracted three times with ether
  3. customThe precipitate which had separated out
  4. filtrationwas filtered off under suction
  5. washwashed with water
  6. customdried in a stream of nitrogen
  7. customRecrystallization from isopropanol

출처 및 근거

ORD 기록
ord-ff463857344f4583b0230bb52beadf68
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05126371

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