Water → Ethyl 5-(2-methyl-5-thiazolyl)-2,4-pentadienoate

HRID 972833ノート

反応式

HRID 972833 の反応式
C(OP(/[C:9](=[CH:15]\[CH3:16])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH3:19][C:20]1[S:21][C:22]([CH:25]=O)=[CH:23][N:24]=1.O>O1CCCC1.CCOCC>[CH3:19][C:20]1[S:21][C:22]([CH:25]=[CH:16][CH:15]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:23][N:24]=1

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 7022350Ethyl diethylphosphonocrotonateHCID 139347282-Methyl-1,3-thiazole-5-carbaldehyde

生成物 1

HCID 54252691Ethyl 5-(2-methyl-5-thiazolyl)-2,4-pentadienoate収率 98.6%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

A solution of 12.5 g of ethyl diethylphosphonocrotonate in 25 ml of tetrahydrofuran was added with stirring to a mixture of 100 ml of anhydrous tetrahydrofuran and 3 g of sodium hydride in 46% of an oil cooled to 0°C and the mixture was stirred for 30 minutes at 0°C. Then, a mixture of 6.4 g of 2-methyl-5-thiazolecarboxaldehyde in 25 ml of tetrahydrofuran was added to the mixture at 0°C and 250 ml of ice and 250 ml of water were added. The mixture was extracted with methylene chloride and the organic extracts were washed with water, dried and filtered. The filtrate was evaporated to dryness under reduced pressure to obtain 13 g of raw product which was dissolved in ether and the ether solution was stirred in the presence of Florosil and then with activated carbon. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure to obtain 11 g of ethyl 5-(2-methyl-5-thiazolyl)-2,4-pentadienoate in the form of a pale yellow oil.

後処理

  1. additionwas added to the mixture at 0°C
  2. extractionThe mixture was extracted with methylene chloride
  3. washthe organic extracts were washed with water
  4. customdried
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness under reduced pressure
  7. customto obtain 13 g of raw product which
  8. filtrationThe mixture was filtered
  9. customthe filtrate was evaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-e9e6cf7cf0514329be9064b9f11e32d7
出典データセット
uspto-grants-1977_10
特許番号
US04053618

反応ノート

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