Ethyl 2-methylbenzo[d]oxazole-7-carboxylate → (2-Methyl-1,3-benzoxazol-7-yl)methanol

HRID 445875ノート

反応式

HRID 445875 の反応式
[CH3:1][C:2]1[O:3][C:4]2[C:10]([C:11](OCC)=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][C:2]1[O:3][C:4]2[C:10]([CH2:11][OH:12])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

参加物

4

反応物 2

HCID 12157468Ethyl 2-methylbenzo[d]oxazole-7-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 58566559(2-Methyl-1,3-benzoxazol-7-yl)methanol収率 68%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of ethyl 2-methylbenzo[d]oxazole-7-carboxylate (743) (1.27 g, 6.19 mmol) in tetrahydrofuran (61 mL) at 0° C. was added lithium aluminum hydride (7.43 mL, 7.43 mmol, 1M in tetrahydrofuran). The reaction was stirred at 0° C. for 1 hour and quenched with 0.6 mL of water, 0.6 mL of 15% NaOH and 1.8 mL of water. The reaction was warmed to room temperature and diluted with diethyl ether. Magnesium sulfate was added and the solution was filtered, washed with diethyl ether, and the solvent was removed in vacuo to provide (2-methylbenzo[d]oxazol-7-yl)methanol (744) (0.687 g, 68%).

後処理

  1. customquenched with 0.6 mL of water, 0.6 mL of 15% NaOH and 1.8 mL of water
  2. temperatureThe reaction was warmed to room temperature
  3. additiondiluted with diethyl ether
  4. additionMagnesium sulfate was added
  5. filtrationthe solution was filtered
  6. washwashed with diethyl ether
  7. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-b3fa9ea86a184523bdfe5ccbc685e6fe
出典データセット
uspto-grants-2013_07
特許番号
US08476308B2

反応ノート

読み込み中…