1,2-Bis(2-chloroethoxy)ethane → 3-{2-[2-(2-Chloroethoxy)ethoxy]ethoxy}-4,5-dimethoxybenzaldehyde

HRID 1510970

反応式

HRID 1510970 の反応式
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[OH:13].Cl[CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][Cl:23].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:13][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:11][CH3:12])[C:3]=1[O:2][CH3:1])[CH:7]=[O:8]

参加物

5

反応物 3

HCID 81711,2-Bis(2-chloroethoxy)ethaneHCID 10796Cesium carbonateHCID 1415133,4-Dimethoxy-5-hydroxybenzaldehyde

生成物 1

HCID 861009263-{2-[2-(2-Chloroethoxy)ethoxy]ethoxy}-4,5-dimethoxybenzaldehyde収率 80%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

A solution of 500 mg (2.75 mmol) 4,5-dimethoxy-3-hydroxybenzaldehyde 1 and 860 μl (1.03 g, 5.50 mmol) 1,2-bis(2-chloroethoxy)ethane in 20 ml DMF was treated with 2.24 g (6.88 mmol) caesium carbonate and heated to 55° C. for 20 hrs. After cooling the mixture was poured into 100 ml of ice water and extracted with chloroform. The organic extracts were washed twice with 50 ml of water and with brine, dried over sodium sulfate and evaporated. The resulting yellow oil was flash-chromatographed (petroleum ether/ethyl acetate 2/1) to yield 3-{2-[2-(2-chloroethoxy)ethoxy]ethoxy}-4,5-dimethoxybenzaldehyde (730 mg, 2.20 mmol, 80%), which was directly used for the next synthesis step.

後処理

  1. temperatureAfter cooling the mixture
  2. extractionextracted with chloroform
  3. washThe organic extracts were washed twice with 50 ml of water and with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe resulting yellow oil was flash-chromatographed (petroleum ether/ethyl acetate 2/1)

出典と根拠

ORDレコード
ord-188516f93ea24b198ee9512e3cd43a0e
出典データセット
uspto-grants-2012_07
特許番号
US08212058B2

関連ノート

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