Dimethylformamide → HCID 19001392、化合物

HRID 2259607

反応式

HRID 2259607 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:10])[CH:3]=1.CN(C=O)C.Br[CH2:17][C:18]([CH:20]=[CH2:21])=[CH2:19].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH2:19][C:18](=[CH2:17])[CH:20]=[CH2:21])[CH:3]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 902381,3-Butadiene, 2-(bromomethyl)-HCID 5201014-Chloro-2-hydroxybenzaldehyde

生成物 1

HCID 19001392HCID 19001392、化合物収率 84.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

To a solution of 4.1 g (0.026 mol) of 4-chloro-2-hydroxybenzaldehyde and 27 mL of DMF was added 5 g (0.034 mol) of 2-bromomethyl-1,3-butadiene and 7.2 g (0.052 mol) of potassium carbonate. The resulting mixture was heated at 70° C. for 4 h and then cooled to room temperature and poured into a mixture of 100 mL of water and 100 mL of methylene chloride. The aqueous layer was extracted with two 100 mL portions of methylene chloride and the combined organic layers were washed twice with 100 mL of water, twice with 100 mL of saturated sodium bicarbonate solution, dried over magnesium sulfate and concentrated to give 4.9 g of an oil. Purification by flash chromatography using 250 g of silica gel and eluting with 10:1 hexanes-EtOAc gave 2.6 g of the desired product. 200 MHz 1H NMR (CDCl3): δ4.82 (s, 2H), 5.18-5.42 (m, 4H), 6.45 (dd, 1H), 7.01 (s, 1H), 7.05 (d, 1H), 7.79 (d, 1H), 10.48 (s, 1H).

後処理

  1. temperaturecooled to room temperature
  2. extractionThe aqueous layer was extracted with two 100 mL portions of methylene chloride
  3. washthe combined organic layers were washed twice with 100 mL of water, twice with 100 mL of saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-f54ce4d81fe24c02a716a1fe9c707d60
出典データセット
uspto-grants-1995_12
特許番号
US05474998

関連ノート

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