Diisobutylaluminum hydride → (4-(Benzo[d]thiazol-2-yl)phenyl)methanol

HRID 1582310

반응식

HRID 1582310 반응식
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1.CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[S:11]1[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=[C:10]1[C:7]1[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 14487Diisobutylaluminum hydrideHCID 71741754-Benzothiazol-2-yl-benzoic acid methyl esterHCID 9855836Potassium sodium tartarate

생성물 1

HCID 17047054(4-(Benzo[d]thiazol-2-yl)phenyl)methanol수율 75%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a 0° C. solution of methyl-4-(benzothiazol-2-yl)-benzoate (prepared as described by A. Brembilla, D. Roizard and P. Lochon Synth. Commun. 1990, 20, 3379) (1.08 g, 4 mmol) in THF (20 mL) was added DIBAL-H (20 mL of a 1.0 M solution in THF, 20 mmol) over 10 minutes. The resulting solution was stirred at 0° C. for 2 hours, then an aqueous saturated solution of sodium potassium tartrate was added and the biphasic mixture stirred rapidly for 60 min. The phases were separated and the aqueous layer extracted with ether (3×20 mL). The combined organic fractions were dried (Na2SO4), concentrated and purified by column chromatography on silica gel (10:1 CH2Cl2/MeOH) to afford the title compound (0.69 g, 75%). 1H NMR (CD3OD) δ4.69 (s, 2H), 7.43 (t, 1H, J=7.8 Hz), 7.53 (m, 3H), 7.99 (m, 1H), 8.06 (m, 3H).

후처리

  1. stirringthe biphasic mixture stirred rapidly for 60 min
  2. customThe phases were separated
  3. extractionthe aqueous layer extracted with ether (3×20 mL)
  4. dry with materialThe combined organic fractions were dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by column chromatography on silica gel (10:1 CH2Cl2/MeOH)

출처 및 근거

ORD 기록
ord-72e06e19a034437a9d7b884feff325bc
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734191B2

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