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

HRID 969567ノート

反応式

HRID 969567 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 590174304-Hydroxy-4-pyrimidin-2-yl-cyclohexanone収率 49.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b9910094fa1441c2bad9ff9976190b46
出典データセット
uspto-grants-2007_12
特許番号
US07307086B2

反応ノート

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