Acetic Acid → HCID 178489653, 화합물

HRID 1471883

반응식

HRID 1471883 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)[CH:6]=[CH:7][CH:8]=1.CC(C)([O-])C.[K+].[C:24](=[S:26])=S.Br[CH2:28][CH2:29][O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1.C(O)(=O)C.O.[NH2:42][NH2:43]>C1COCC1.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:42][NH:43][C:24]=2[S:26][CH2:28][CH2:29][O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH:6]=[CH:7][CH:8]=1

참가 물질

9

반응물 6

HCID 176Acetic AcidHCID 6348Carbon DisulfideHCID 24654Hydrazine hydrate (1:1)HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 27596142-(3-Methoxyphenyl)-1-phenylethan-1-oneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 178489653HCID 178489653, 화합물수율 74.2%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 2-(3-methoxyphenyl)-1-phenylethanone (1.25 g, 5.52 mmol) in THF (11.05 mL) was added potassium tert-butoxide (11.49 mL, 11.49 mmol). After 30 min, CS2 (0.363 mL, 6.02 mmol) was added and the mixture was stirred for 10 min before 2-(2-bromoethoxy)tetrahydro-2H-pyran (2.086 mL, 13.81 mmol) was added and the reaction was stirred overnight. The mixture was diluted with ethanol (11.05 mL). Acetic acid (1.898 mL, 33.1 mmol) was added followed by hydrazine hydrate (2.71 mL, 55.2 mmol). The reaction was stirred at 85° C. overnight and concentrated under reduced pressure. The residue was extracted with EtOAc/H2O (twice). The organic phases were combined and washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a white solid (1.681 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.52-1.64 (m, 3H), 1.65-1.93 (m, 3H), 3.06 (t, J=5.94 Hz, 2H), 3.49-3.57 (m, 1H), 3.65-3.71 (m, 1H), 3.72 (s, 3H), 3.88-3.95 (m, 1H), 3.97-4.05 (m, 1H), 4.66-4.69 (m, 1H), 6.79-6.90 (m, 3H), 7.19-7.26 (m, 1H), 7.26-7.33 (m, 3H), 7.37-7.45 (m, 2H), 10.91 (bs, 1H).

후처리

  1. additionwas added
  2. stirringThe reaction was stirred at 85° C. overnight
  3. concentrationconcentrated under reduced pressure
  4. extractionThe residue was extracted with EtOAc/H2O (twice)
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-2eb3ade9b8fa4674a7a9e4d78e88bc0e
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012478B2

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