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

HRID 278449ノート

反応式

HRID 278449 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-cbcb01bf856d47a7917da13fea8e44e8
出典データセット
uspto-grants-2002_03
特許番号
US06359138B1

反応ノート

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