Diisopropylamine → HCID 14233936, 화합물

HRID 1590454

반응식

HRID 1590454 반응식
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][O:14][C:15]1[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH:16]=1.Cl[CH2:23][C:24]1[N:25]=[CH:26][N:27]([C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:28]=1[CH3:29].C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:13][O:14][C:15]1[CH2:20][CH2:19][CH:18]([CH2:23][C:24]2[N:25]=[CH:26][N:27]([C:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:28]=2[CH3:29])[C:17](=[O:21])[CH:16]=1

참가 물질

7

반응물 5

HCID 7912DiisopropylamineHCID 855973-Methoxycyclohex-2-en-1-oneHCID 516892Sodium BicarbonateHCID 110469654-(Chloromethyl)-5-methyl-1-trityl-1H-imidazoleHCID 178418339Butyllithium

생성물 1

HCID 14233936HCID 14233936, 화합물수율 104.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

n-Butyllithium (1.58 M in hexane; 21 ml) was added at -78° under nitrogen to a stirred solution of diisopropylamine (4.6 ml) in dry THF (75 ml) and the solution was stirred at 0° for 30 min. The solution was cooled to -78° and added to a solution of 3-methoxy-2-cyclohexen-1 one (3.4 g) in dry THF (25 ml) at -78° under nitrogen with stirring. After stirring for 1 h at -78° and for 30 min. at 0° the solution was cooled to -78° and a solution of 4-(chloromethyl)-5-methyl-1 -(triphenylmethyl)-1H-imidazole (10 g) in dry THF (100 ml) was added dropwise with stirring under nitrogen. The solution was stirred at -78° for 3 h and at 0° for 30 min., treated with 8% aqueous sodium bicarbonate (400 ml) and extracted with ethyl acetate (2×300 ml). The combined, dried organic extracts were evaporated to give an oil (ca. 13 g) which was purified by SPCC eluting with System A (967:30:3) to give the title compound (3.28 g), m.p. 145°-148°.

후처리

  1. temperatureThe solution was cooled to -78°
  2. stirringwith stirring
  3. stirringAfter stirring for 1 h at -78° and for 30 min. at 0° the solution
  4. temperaturewas cooled to -78°
  5. stirringwith stirring under nitrogen
  6. stirringThe solution was stirred at -78° for 3 h and at 0° for 30 min.
  7. extractionextracted with ethyl acetate (2×300 ml)
  8. customdried organic extracts were evaporated

출처 및 근거

ORD 기록
ord-91621d1bdaed4135833c24ffab1ece67
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05202343

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