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

HRID 425763

反応式

HRID 425763 の反応式
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]=[C:8]2[Cl:15])=O.CC(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:2])[CH:6]=2)[N:11]=[CH:10][N:9]=1

参加物

4

反応物 2

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

生成物 1

HCID 57469640(4-Chloroquinazolin-6-yl)methanol収率 68.5%

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, 0.015 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-chloroquinazoline-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-ebf3c2ba782f47bf838d1fa2bf29ff02
出典データセット
uspto-grants-2012_01
特許番号
US08106214B2

関連ノート

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