Diisobutylaluminum hydride → (4-Chloroquinolin-6-yl)methanol

HRID 2261084

反応式

HRID 2261084 の反応式
CO[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10]N=[C:8]2[Cl:15])=[O:4].[CH3:16]C(C[AlH]CC(C)C)C>C1COCC1>[Cl:15][C:8]1[C:7]2[C:12](=[CH:13][CH:14]=[C:5]([CH2:3][OH:4])[CH:6]=2)[N:11]=[CH:10][CH:16]=1

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 18925080Methyl 4-chloroquinazoline-6-carboxylate

生成物 1

HCID 57469641(4-Chloroquinolin-6-yl)methanol収率 66%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

To a solution of methyl-4-chloroquinazoline-6-carboxylate (3.5 g, 0015 mol) in dry THF (35 mL) at −25° C. was added DIBAL-H (4.4 g, 0.031 mol) and stirred at −25° C. to RT for 2 h. The reaction mixture was cooled to −10° C. and quenched with 10% aqueous NaHCO3 (9 mL). The reaction mixture was extracted with ethylacetate (100 mL), washed with water, brine and dried. The solvent was removed under vacuum to give 4-chloroquinoline-6-yl methanol (2 g, 66%).

後処理

  1. customquenched with 10% aqueous NaHCO3 (9 mL)
  2. extractionThe reaction mixture was extracted with ethylacetate (100 mL)
  3. washwashed with water, brine
  4. customdried
  5. customThe solvent was removed under vacuum

出典と根拠

ORDレコード
ord-d4d4fdbbdfd34863a9f143cfbff3d516
出典データセット
uspto-grants-2010_12
特許番号
US07846925B2

関連ノート

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