1,4-Dioxaspiro[4.5]decan-8-one → 8-Pyrimidin-2-yl-1,4-dioxa-spiro[4.5]decan-8-ol

HRID 1025768노트

반응식

HRID 1025768 반응식
[SnH3][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[O:13]1[C:17]2([CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1>C1COCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[C:20]1([OH:23])[CH2:21][CH2:22][C:17]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:18][CH2:19]1

참가 물질

5

반응물 3

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 871506562-Stannyl pyrimidineHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 2-stannyl pyrimidine (200 mmol, 80 g), prepared as previously described in the literature (Tetrahedron, 1994, 50, 275-284), in THF (1 L) was added n-butyllithium (240 mmol, 150 mL) at −78° C. The reaction was stirred for 30 min at −78° C. and 1,4-dioxa-spiro[4.5]decan-8-one (200 mmol, 30 g) was added. The reaction was allowed to stir overnight while warming to ambient temperature. The reaction was then quenched using NH4Cl and extracted using EtOAc (3×400 mL). The organic layers were combined and dried over MgSO4 and concentrated in vacuo. The crude was taken to the next step.

후처리

  1. stirringto stir overnight
  2. temperaturewhile warming to ambient temperature
  3. customThe reaction was then quenched
  4. extractionextracted
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b4caa8034f4841e9b58831922ba3357a
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729063B2

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