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

HRID 1876433노트

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HRID 1876433 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-78c0e43157124013bee72027fe44daf5
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309600B2

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