Sodium hydride → 3-(3-Benzyloxy-propoxy)-5-chloro-2-hydroxy-benzaldehyde

HRID 2367997ノート

反応式

HRID 2367997 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[H-].[Na+].[CH2:14]([O:21][CH2:22][CH2:23][CH2:24]Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CS(C)=O>[CH2:14]([O:21][CH2:22][CH2:23][CH2:24][O:11][C:4]1[C:5]([OH:10])=[C:6]([CH:9]=[C:2]([Cl:1])[CH:3]=1)[CH:7]=[O:8])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 2776064Benzyl 3-Bromopropyl EtherHCID 219248625-Chloro-2,3-dihydroxybenzaldehyde

生成物 1

HCID 866647393-(3-Benzyloxy-propoxy)-5-chloro-2-hydroxy-benzaldehyde収率 94%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 5-chloro-2,3-dihydroxy-benzaldehyde (3.1 g, 17.7 mmol) in anhydrous DMSO (20 mL) was added NaH (60% in mineral oil, 1.50 g, 35.4 mmol) portion-wise and the mixture was stirred for 30 minutes. The solution was cooled to 0° C. and a solution of 3-benzyloxy-1-bromopropane (3.1 mL, 17.7 mmol) in DMSO (3 mL) was added dropwise over 10 minutes period. The ice bath was removed. After overnight, the solution was diluted with EtOAc (100 mL), washed with water, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The product was purified by silica gel column chromatography (2:1 hexanes-EtOAc mobile phase) generating the title compound (5.3 g, 16.6 mmol, 94%) as a light yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.81 (s, 1H), 9.87 (s, 1H), 7.42-7.28 (m, 5H), 7.17 (s, 1H), 7.08 (s, 1H), 4.53 (s, 2H), 4.17 (t, J=6.2 Hz, 2H), 3.69 (t, J=5.8 Hz, 2H), 2.15 (t, J=6.2 Hz, 2H).

後処理

  1. customThe ice bath was removed
  2. waitAfter overnight
  3. additionthe solution was diluted with EtOAc (100 mL)
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe product was purified by silica gel column chromatography (2:1 hexanes-EtOAc mobile phase)

出典と根拠

ORDレコード
ord-34fb0cb475be467596a76b3626ffdabd
出典データセット
uspto-grants-2014_04
特許番号
US08703742B2

反応ノート

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