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

HRID 2264143

反応式

HRID 2264143 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f4145d78c7d3416390d338d79fdb3716
出典データセット
uspto-grants-2010_12
特許番号
US07855201B2

関連ノート

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