2,3-dihydro-1,4-benzodioxin-5-ylmethanol → 2,3-Dihydro-1,4-benzodioxine-5-carbaldehyde

HRID 1174671ノート

反応式

HRID 1174671 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][OH:12])[C:5]=2[O:4][CH2:3][CH2:2]1>C1COCC1.[O-2].[Mn+4].[O-2].O=[Mn]=O>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]=[O:12])[C:5]=2[O:4][CH2:3][CH2:2]1

参加物

5

反応物 1

HCID 27761822,3-dihydro-1,4-benzodioxin-5-ylmethanol2 回

生成物 1

HCID 27950332,3-Dihydro-1,4-benzodioxine-5-carbaldehyde収率 88%

試薬・触媒・溶媒 3

HCID 14801Manganese dioxide触媒HCID 178418406HCID 178418406、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

A solution of 2,3-dihydro-1,4-benzodioxin-5-ylmethanol (Intermediate A1) (commercially available from Aldrich) (3 g, 18.1 mmol) in THF (100 mL) was treated with manganese(IV) oxide, activated (commercially available from Aldrich): MnO2 (10 g, 115 mmol) at rt. The mixture was heated to 35° C. for 2 h and 60° C. for 4 h followed by 18 h at room temperature (rt). The mixture was filtered through celite and the solvent was removed under vacuum. The residue was purified by chromatography on silica gel with 20% EtOAc: hexanes to give 2,3-dihydro-benzo[1,4]dioxine-5-carbaldehyde (Intermediate A2) 2.6 g (88%).

後処理

  1. customat rt
  2. custom(rt)
  3. filtrationThe mixture was filtered through celite
  4. customthe solvent was removed under vacuum
  5. customThe residue was purified by chromatography on silica gel with 20% EtOAc

出典と根拠

ORDレコード
ord-9be0b0b968f541abab89ed52802cf6f7
出典データセット
uspto-grants-2010_11
特許番号
US07838545B2

反応ノート

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