Water → 4-(2,2-diethoxyethyl)-2,3-dihydrothieno[3,2-f]1,4-thiazepin-5(4H)-one

HRID 847387ノート

反応式

HRID 847387 の反応式
[S:1]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[C:5](=[O:11])[NH:4][CH2:3][CH2:2]1.CC(C)([O-])C.[K+].[CH2:18]([O:20][CH:21]([O:24][CH2:25][CH3:26])[CH2:22]Br)[CH3:19].O>CN(C)C=O>[CH2:18]([O:20][CH:21]([O:24][CH2:25][CH3:26])[CH2:22][N:4]1[C:5](=[O:11])[C:6]2[CH:10]=[CH:9][S:8][C:7]=2[S:1][CH2:2][CH2:3]1)[CH3:19]

参加物

6

反応物 4

HCID 962WaterHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 43659423,4-dihydrothieno[3,2-f][1,4]thiazepin-5(2H)-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 198810924-(2,2-diethoxyethyl)-2,3-dihydrothieno[3,2-f]1,4-thiazepin-5(4H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 8.0 g of 2,3-dihydrothieno[3,2-f]-1,4-thiazepin-5(4H)-one in 160 ml of N,N-dimethylformamide was added 6.3 g of potassium t-butoxide with stirring under ice-cooling and the mixture was stirred for an hour at room temperature. Then to the mixture was added 8.4 ml of bromoacetaldehyde diethyl acetal under ice-cooling. The mixture was stirred for 5 hours at room temperature and water was added thereto and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and the solvent was distilled off. The residue was chromatographed on a silica gel using and chloroform and methanol (98.8:0.2) as an eluent to give 6,9 g of 4-(2,2-diethoxyethyl)-2,3-dihydrothieno[3,2-f]1,4-thiazepin-5(4H)-one as a pale yellow oil. To the solution of thus obtained 6.7 g of 4-(2,2-diethoxyethyl)-2,3-dihydrothieno[3,2-f]-1,4-thiazepin-5(4H)-one in 150 ml of tetrahydrofuran was added 20 ml of 10% hydrochloric acid and the mixture was allowed to stand for 20 hours at room temperature, and then poured into water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and the solvent was distilled off to give 4.4 g of 2,3,4,5-tetrahydro-5-oxothieno[3,2-f]-1,4-thiazepin-4-acetaldehyde as a pale yellow oil.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred for an hour at room temperature
  3. temperaturecooling
  4. stirringThe mixture was stirred for 5 hours at room temperature
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customThe residue was chromatographed on a silica gel using and chloroform and methanol (98.8:0.2) as an eluent

出典と根拠

ORDレコード
ord-143a236a8264443da174a1b41d54389f
出典データセット
uspto-grants-1992_08
特許番号
US05141930

反応ノート

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