Sodium Hydroxide → 6-(Hydroxymethyl)benzothiazole

HRID 911324

반응식

HRID 911324 반응식
C[O:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]2[N:9]=[CH:10][S:11][C:7]=2[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[S:11]1[C:7]2[CH:6]=[C:5]([CH2:3][OH:2])[CH:13]=[CH:12][C:8]=2[N:9]=[CH:10]1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 595763Methyl benzo[d]thiazole-6-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 178603856-(Hydroxymethyl)benzothiazole수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-10 °C

실험 절차

Add slowly a solution of benzothiazole-6-carboxylic acid methyl ester (0.5 g, 2.59 mmol) in anhydrous THF (10 mL) to a suspension of lithium aluminum hydride (0.1 g, 2.85 mmol) in anhydrous THF (20 mL) at −10° C. and stir for 20 min at −10° C. Treat the reaction mixture with 2N aqueous NaOH until a granular precipitate starts to form and filter through a pad of Celite®. Evaporate the solvent and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1, 7:3, 3:2 and 1:1) to obtain the desired intermediate as a yellow oil (0.4 g, 99%). MS (ES+) m/z: 166 (M+H)+.

후처리

  1. customto form
  2. filtrationfilter through a pad of Celite®
  3. customEvaporate the solvent
  4. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1, 7:3, 3:2 and 1:1)

출처 및 근거

ORD 기록
ord-ddcd779d55db429da89e393769149eb4
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

연결된 노트

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