Acetone → 2-(2-nitrophenyl)-Thiazolo[5,4-b]pyridine-6-methanol

HRID 453279ノート

反応式

HRID 453279 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([C:19](OC)=[O:20])=[CH:14][N:13]=2)([O-:3])=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].CC(C)=O.[O-]S([O-])=O.[Na+].[Na+]>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([CH2:19][OH:20])=[CH:14][N:13]=2)([O-:3])=[O:2]

参加物

6

反応物 4

HCID 180AcetoneHCID 24437Sodium SulfiteHCID 21226445Aluminium lithium hydrideHCID 58551887Methyl 2-(2-nitrophenyl)thiazolo[5,4-b]pyridine-6-carboxylate

生成物 1

HCID 573471802-(2-nitrophenyl)-Thiazolo[5,4-b]pyridine-6-methanol収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-60 °C

実験手順

A solution of methyl 2-(2-nitrophenyl)thiazolo[5,4-b]pyridine-6-carboxylate (1 eq) in THF was added over 8 h to a mixture of lithium aluminum hydride (LAH) (4.4 eq) in THF maintaining the internal temperature at −55° C. The reaction mixture was stirred an additional 4 h at −60° C. Acetone (18 eq) was added followed by sat. aq Na2SO3. The resultant solids were removed by filtration and rinsed with THF. The combined organics were concentrated in vacuo and the crude residue crystallized from CH2Cl2 to give (2-(2-nitrophenyl)thiazolo[5,4-b]pyridin-6-yl)methanol (50% yield).

後処理

  1. customThe resultant solids were removed by filtration
  2. washrinsed with THF
  3. concentrationThe combined organics were concentrated in vacuo
  4. customthe crude residue crystallized from CH2Cl2

出典と根拠

ORDレコード
ord-08a366e350b048b09465e04033542f3f
出典データセット
uspto-grants-2013_07
特許番号
US08492401B2

反応ノート

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