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

HRID 1174671노트

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HRID 1174671 반응식
[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

참가 물질

5

반응물 1

HCID 27761822,3-dihydro-1,4-benzodioxin-5-ylmethanol2회

생성물 1

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

시약·촉매·용매 3

HCID 14801Manganese dioxide촉매HCID 178418406HCID 178418406, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-9be0b0b968f541abab89ed52802cf6f7
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838545B2

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