Sodium Hydroxide → (6-Methoxy-2,3-dihydro-1-benzofuran-2-yl)methanol

HRID 278449노트

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HRID 278449 반응식
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH:8]([C:10](O)=[O:11])[O:9][C:5]=2[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.CCOC(C)=O.O>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH:8]([CH2:10][OH:11])[O:9][C:5]=2[CH:4]=1

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 109978826-Methoxy-2,3-dihydro-1-benzofuran-2-carboxylic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 22628398(6-Methoxy-2,3-dihydro-1-benzofuran-2-yl)methanol수율 70%

시약·촉매·용매 3

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A solution of (RS)-6-methoxy-2,3-dihydro-benzofuran-2-carboxylic acid (158 mg, 0.813 mmol) in THF (2 ml) was added dropwise in a 0° C. suspension of LiAlH4 (31 mg, 0.813 mmol) in THF (2 ml). After 30 min stirring at 0° C., the reaction mixture was allowed to reflux for 30 minutes. The reaction mixture was then cooled to 0° C. and treated successively with H2O (0.05 ml), 5N NaOH (0.05 ml), H2O (0.15 ml). After 20 minutes stirring at room temperature, EtOAc was added followed by Na2SO4. The so obtained solid was filtered and the filtrate was evaporated. The residue was chromatographed over SiO2 (Merck 230-400 mesh) eluting with nHexane-EtOAc (4:1) to provide (RS)-(6-methoxy-2,3-dihydro-benzofuran-2-yl)-methanol (102 mg, 70%) as a colorless oil, MS:m/e=180 (M+).

후처리

  1. temperatureto reflux for 30 minutes
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. stirringAfter 20 minutes stirring at room temperature
  4. customThe so obtained solid
  5. filtrationwas filtered
  6. customthe filtrate was evaporated
  7. customThe residue was chromatographed over SiO2 (Merck 230-400 mesh)
  8. washeluting with nHexane-EtOAc (4:1)

출처 및 근거

ORD 기록
ord-cbcb01bf856d47a7917da13fea8e44e8
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06359138B1

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