Benzaldehyde, 4-(phenylmethoxy)- → HCID 16722958、化合物

HRID 730385ノート

反応式

HRID 730385 の反応式
[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]

参加物

7

反応物 5

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-2 回HCID 136177(2-Cyanoethyl)hydrazineHCID 521998p-Toluenesulfonic acid monohydrate2 回HCID 5003444Sodium cyanoborohydride2 回HCID 57594128HCID 57594128、化合物

生成物 1

HCID 16722958HCID 16722958、化合物収率 61.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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, 1 H) 7.45 (dd, J=8.8, 2.2 Hz, 2 H) 7.42 (s, 1 H) 7.36-7.41 (m, 2 H) 7.32 (tt, J=7.0, 1.8 Hz, 1 H) 7.28 (s, 1 H) 7.17 (br. s., 1 H) 6.94 (d, J=8.6 Hz, 2 H) 6.88 (d, J=8.6 Hz, 1 H) 5.05 (s, 2 H) 4.61 (qq, J=6.0 Hz, 1 H) 4.22 (s, 2 H) 3.39 (t, J=6.6 Hz, 2 H) 2.60 (t, J=6.6 Hz, 2 H) 1.39 (d, J=6.1 Hz, 6 H) 4.22 (s, 2 H) 3.39 (t, J=6.6 Hz, 2 H) 2.60 (t, J=6.6 Hz, 2 H) 1.39 (d, J=6.1 Hz, 6 H). MS(ES+) m/e 478 [M+H]+.

後処理

  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)

出典と根拠

ORDレコード
ord-7a38f0c4d7694bc7be1c7c72f63483c2
出典データセット
uspto-grants-2009_09
特許番号
US07582668B2

反応ノート

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