Isopropyl Acetate → HCID 16680143, 화합물

HRID 968877노트

반응식

HRID 968877 반응식
CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([C:28]2([C:35]3[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=3[F:42])[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(OC(C)C)(=O)C>O1CCCC1.O>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([C:28]2([C:35]3[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=3[F:42])[CH2:29][CH2:30][C:31](=[CH:9][C:7]#[N:8])[CH2:32][CH2:33]2)(=[O:26])=[O:27])=[CH:23][CH:24]=1

참가 물질

7

반응물 4

HCID 7915Isopropyl AcetateHCID 75676Diethyl (cyanomethyl)phosphonateHCID 104301374-(4-chlorophenyl)sulfonyl-4-(2,5-difluorophenyl)cyclohexan-1-oneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 16680143HCID 16680143, 화합물수율 87.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of potassium tert butoxide (1.0M in THF, 3.20 Kg, 3.55 mol) in tetrahydrofuran (2.1L) was added diethyl (cyanomethyl)phosphonate (642 g, 3.62 mol), maintaining the temperature below 5° C. The resulting solution was aged for 2 h and a solution of 4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexanone (1.07 Kg, 2.78 mol) (Preparation 2) in tetrahydrofuran (3.9 L) was added. After the reaction was completed, isopropyl acetate (13.1 L) and water (26.3 L) were added. The organic layer was washed with brine and then concentrated to 1 L. Heptane (10.5 L) was added. The resulting solid was filtered, washed with heptane, dried in vacuo at 37° C. and then slurried in diethyl ether (5 L). Filtration and drying in vacuo afforded 989 g (87% yield) of [4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexylidene]acetonitrile. 1H NMR (CDCl3) 7.41-7.34 (4H, m), 7.25-7.06 (2H, m), 6.94-6.87 (1H, m), 5.12 (1H, s), 3.05-3.03 (1H, m), 2.92-2.86 (2H, m), 2.54-2.50 (1H, m), and 2.30-2.03 (4H, m).

후처리

  1. temperaturemaintaining the temperature below 5° C
  2. washThe organic layer was washed with brine
  3. concentrationconcentrated to 1 L
  4. additionHeptane (10.5 L) was added
  5. filtrationThe resulting solid was filtered
  6. washwashed with heptane
  7. customdried in vacuo at 37° C.
  8. filtrationFiltration
  9. customdrying in vacuo

출처 및 근거

ORD 기록
ord-ecef6557fef14a458a1e4f772821e5bb
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304094B2

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