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

HRID 1582310

反応式

HRID 1582310 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-72e06e19a034437a9d7b884feff325bc
出典データセット
uspto-grants-2004_05
特許番号
US06734191B2

関連ノート

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