1,3-Dibromopropane → 3,4-dihydro-2H-1,5-benzodioxepine-7-carbaldehyde

HRID 2264143

반응식

HRID 2264143 반응식
O[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].Br[CH2:12][CH2:13][CH2:14]Br.C(=O)([O-])[O-:17].[Cs+].[Cs+]>C(#N)C>[O:17]1[C:9]2[CH:2]=[CH:3][C:4]([CH:5]=[O:6])=[CH:7][C:8]=2[O:10][CH2:14][CH2:13][CH2:12]1

참가 물질

5

반응물 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 943653,5-Dihydroxybenzaldehyde

생성물 1

HCID 27763883,4-dihydro-2H-1,5-benzodioxepine-7-carbaldehyde

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

A mixture of 35 g of 3,5-dihydroxybenzaldehyde, 50 g (0.97 equiv) of 1,3-dibromopropane and 127 g (1.5 equiv) of cesium carbonate in 1 L of anhydrous acetonitrile was heated under nitrogen to 60° C. overnight. The mixture was allowed to cool, then filtered and concentrated under reduced pressure. The residue was partitioned between 500 mL of ethyl acetate and 100 mL of saturated sodium carbonate then dried over magnesium sulfate and concentrated under reduced pressure. Purification by flash chromatography (0-20% ethyl acetate in hexanes) gave the product as clear oil. MS (m+1)=179.1; 1H NMR (400 MHz, CDCl3) 9.82 (s, 1H), 7.42 (m, 2H), 7.02 (m, 1H), 4.32 (t, 2H), 4.24 (t, 2H), 2.22 (m, 2H).

후처리

  1. temperatureto cool
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between 500 mL of ethyl acetate and 100 mL of saturated sodium carbonate
  5. dry with materialthen dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography (0-20% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-f4145d78c7d3416390d338d79fdb3716
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855201B2

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