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

HRID 1799093노트

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HRID 1799093 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-648cd71498164daca865e58763ac91a7
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343997B2

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