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

HRID 1809927ノート

反応式

HRID 1809927 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cffa095ccb824c3dab881afe57c24850
出典データセット
uspto-grants-2013_01
特許番号
US08362003B2

反応ノート

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