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Sodium Hydroxide → 5-Chloro-2-[[(2S)-2-hydroxy-3-(trityloxy)propyl]oxy]benzonitrile

HRID 1160475
ノート
印刷プレビュー

反応式

HRID 1160475 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[C:11]([O:30][CH2:31][C@@H:32]1[CH2:34][O:33]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)([O-])C.[K+].[OH-].[Na+]>C1(C)C=CC=CC=1.COCCOCCOC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:34][C@H:32]([OH:33])[CH2:31][O:30][C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:6]([CH:9]=1)[C:7]#[N:8]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 27774205-Chloro-2-hydroxybenzonitrileHCID 7168113(S)-Glycidyl Trityl EtherHCID 23665647Potassium tert-butoxide

生成物 1

HCID 684202295-Chloro-2-[[(2S)-2-hydroxy-3-(trityloxy)propyl]oxy]benzonitrile収率 85%

試薬・触媒・溶媒 2

HCID 1140
Toluene
溶媒
HCID 8150Diglyme溶媒

反応条件

温度
105 °C

実験手順

To a diglyme (1.1 L) solution of 5-chloro-2-hydroxybenzonitrile (the compound of Reference Example 1; 270 g, 1.8 mol) and (2S)-2-[(trityloxy)methyl]oxirane (465 g, 1.47 mol) was added potassium tert-butoxide (33 g, 0.29 mol) at room temperature, followed by stirring the reaction mixture at 105° C. for 23 hours. The reaction mixture was cooled with ice, to which toluene (2 L) and a 1N sodium hydroxide aqueous solution (1.35 L) were then added to separate an organic layer. The organic layer was washed 3 times each sequentially with the 1N sodium hydroxide aqueous solution (1.35 L) and warm water (3 L), followed by vacuum concentration. Toluene (3 L) was added to the concentrate, to dissolved it, followed by cooling and filtering the precipitated crystal to obtain 590 g of the title compound (yield: 85%).

後処理

  1. customto separate an organic layer
  2. washThe organic layer was washed 3 times each sequentially with the 1N sodium hydroxide aqueous solution (1.35 L)
  3. temperaturewarm water (3 L)
  4. concentrationfollowed by vacuum concentration
  5. additionToluene (3 L) was added to the concentrate
  6. dissolutionto dissolved it
  7. temperatureby cooling
  8. filtrationfiltering the precipitated crystal

出典と根拠

ORDレコード
ord-94c1de99ff704bcd84489c6b27aafbdc
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07816405B2

反応ノート

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