Ammonium Chloride → 2,2-Dimethyl-3-hydroxy-3-(3-methyl-pent-1-yne-1-yl)-4-(1,2,4-triazol-1-yl)-butane

HRID 358930

반응식

HRID 358930 반응식
C([Mg]Br)C.[CH3:5][CH:6]([CH2:9][CH3:10])[C:7]#[CH:8].[CH3:11][C:12]([CH3:22])([C:14](=[O:21])[CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[CH3:13].[Cl-].[NH4+]>C(OCC)C.ClCCl>[CH3:13][C:12]([CH3:22])([C:14]([OH:21])([C:8]#[C:7][CH:6]([CH3:5])[CH2:9][CH3:10])[CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[CH3:11]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 1008773,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanoneHCID 1367043-Methyl-1-pentyneHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 137871212,2-Dimethyl-3-hydroxy-3-(3-methyl-pent-1-yne-1-yl)-4-(1,2,4-triazol-1-yl)-butane

시약·촉매·용매 2

HCID 3283Diethyl Ether용매3회HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

10 To a solution of ethyl magnesium bromide (20 ml) of a 3M solution in diethyl ether) in dry diethyl ether (30 ml) under N2 at room temperature was added a solution of 3-methyl-1-pentyne (5 g, 0.06 mol) in diethyl ether (20 ml). The resulting mixture was heated under reflux for 1 hour, and then cooled to 0° C. To this mixture was added slowly a solution of 2,2-dimethyl-4-(1,2,4-triazol-1-yl)-butane-3-one (8.4 g, 0.05 mol) in dry dichloromethane (150 ml), and the mixture stirred for 45 minutes, a gelatinous precipitate formed. Ammonium chloride solution was added to the mixture, and the organic layer separated and washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica eluting with diethyl ether (20-100%) in petrol gave 2,2-dimethyl-3-hydroxy-3-(3-methyl-pent-1-yne-1-yl)-4-(1,2,4-triazol-1-yl)-butane) as a white solid (4.29 g) (mpt=59°-60° C.).

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customa gelatinous precipitate formed
  4. customthe organic layer separated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica eluting with diethyl ether (20-100%) in petrol

출처 및 근거

ORD 기록
ord-df759c25482744f88b06d374d8e81863
출처 데이터셋
uspto-grants-1991_03
특허 번호
US04999043

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