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

HRID 1160475
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HRID 1160475 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 1140
Toluene
용매
HCID 8150Diglyme용매

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온도
105 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-94c1de99ff704bcd84489c6b27aafbdc
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07816405B2

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