Hydrochloric Acid → 4-Hydroxy-4-pyrimidin-2-yl-cyclohexanone

HRID 969567노트

반응식

HRID 969567 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1([OH:17])[CH2:16][CH2:15][C:10]2(OCC[O:11]2)[CH2:9][CH2:8]1.Cl>C1COCC1>[OH:17][C:7]1([C:2]2[N:1]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:16][CH2:15][C:10](=[O:11])[CH2:9][CH2:8]1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 590174338-Pyrimidin-2-yl-1,4-dioxa-spiro[4.5]decan-8-ol

생성물 1

HCID 590174304-Hydroxy-4-pyrimidin-2-yl-cyclohexanone수율 49.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To the product from step A (190 mmol, 44 g) in THF (200 mL) was added aqueous HCl solution (300 mmol, 100 mL). The reaction was stirred over 2 days and extracted using diethyl ether. The aqueous layer was then neutralized using aqueous NaOH (50%) to obtain a pH of 11 and extracted using EtOAc (6×300 mL). The organic layers were combined and dried over MgSO4 and concentrated in vacuo. The residue was purified via flash chromatography on silica to afford the desired ketone (18 g, 49%). MS (M+H)+193.1.

후처리

  1. extractionextracted
  2. customto obtain a pH of 11
  3. extractionextracted
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via flash chromatography on silica

출처 및 근거

ORD 기록
ord-b9910094fa1441c2bad9ff9976190b46
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07307086B2

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