Benzaldehyde, 4-(phenylmethoxy)- → HCID 16722958, 화합물

HRID 1697843노트

반응식

HRID 1697843 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[O:22][CH:23]([CH3:25])[CH3:24])[C:5](OC1C(F)=C(F)C(F)=C(F)C=1F)=[O:6].[NH:26]([CH2:28][CH2:29][C:30]#[N:31])[NH2:27].[CH2:32]([O:39][C:40]1[CH:47]=[CH:46][C:43]([CH:44]=O)=[CH:42][CH:41]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C([BH3-])#N.[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[O:22][CH:23]([CH3:25])[CH3:24])[C:5]([NH:27][N:26]([CH2:28][CH2:29][C:30]#[N:31])[CH2:44][C:43]1[CH:46]=[CH:47][C:40]([O:39][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:41][CH:42]=1)=[O:6]

참가 물질

7

반응물 5

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-2회HCID 136177(2-Cyanoethyl)hydrazineHCID 521998p-Toluenesulfonic acid monohydrate2회HCID 5003444Sodium cyanoborohydride2회HCID 57594128HCID 57594128, 화합물

생성물 1

HCID 16722958HCID 16722958, 화합물수율 61.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of pentafluorophenyl 3-chloro-4-[(1-methylethyl)oxy]benzoate (0.100 g, 0.263 mmol) in methanol (5.0 mL) was treated with 3-hydrazinopropanenitrile (0.023 mL, 0.289 mmol) and heated to reflux for 1 h. Following cooling, 4-(benzyloxy)benzaldehyde (0.067 g, 0.315 mmol), sodium cyanoborohydride (0.020 g, 0.315 mmol), and p-toluenesulfonic acid monohydrate (0.060 g, 0.315 mmol) were added and the solution stirred 30 min. at ambient temperature. Additional 4-(benzyloxy)benzaldehyde (0.067 g, 0.315 mmol), sodium cyanoborohydride (0.040 g, 0.637 mmol), and p-toluenesulfonic acid monohydrate (0.100 g, 0.526 mmol) were added and the solution stirred overnight at ambient temperature. The reaction was quenched with 6N aqueous NaOH, diluted with brine, and extracted thrice with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. Purification via flash column chromatography (30-80% EtOAc/hexanes) gave the title compound as a white solid (0.077 g; 61%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.61 (d, J=2.3 Hz, 1H) 7.45 (dd, J=8.8, 2.2 Hz, 2H) 7.42 (s, 1H) 7.36-7.41 (m, 2H) 7.32 (tt, J=7.0, 1.8 Hz, 1H) 7.28 (s, 1H) 7.17 (br. s., 1H) 6.94 (d, J=8.6 Hz, 2H) 6.88 (d, J=8.6 Hz, 1H) 5.05 (s, 2H) 4.61 (qq, J=6.0 Hz, 1H) 4.22 (s, 2H) 3.39 (t, J=6.6 Hz, 2H) 2.60 (t, J=6.6 Hz, 2H) 1.39 (d, J=6.1 Hz, 6H). MS (ES+) m/e 478 [M+H]+.

후처리

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. temperatureFollowing cooling
  4. stirringthe solution stirred overnight at ambient temperature
  5. customThe reaction was quenched with 6N aqueous NaOH
  6. additiondiluted with brine
  7. extractionextracted thrice with EtOAc
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification via flash column chromatography (30-80% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-4d0f17ede6c548188e55d96ce21def53
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163919B2

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