Dimethyl Sulfoxide → 5-Methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carbaldehyde

HRID 1158882ノート

反応式

HRID 1158882 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][N:12]1[CH2:17][CH2:16][C:15]2[S:18][C:19]([CH2:21][OH:22])=[CH:20][C:14]=2[CH2:13]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:11][N:12]1[CH2:17][CH2:16][C:15]2[S:18][C:19]([CH:21]=[O:22])=[CH:20][C:14]=2[CH2:13]1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21941480(5-Methyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridin-2-yl)-methanol

生成物 1

HCID 219414655-Methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carbaldehyde収率 45.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
50 °C

実験手順

DMSO (1.7 ml, 24 mmol) in 5 ml CH2Cl2 was cooled to −50-60° C. Oxalyl chloride (1 ml, 11 mmol) in 20 ml DCM was then added within 5 minutes at 50° C. The mixture was kept at −50° C. for 5 minutes and then 1.67 gram (9 mmol) of (5-Methyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridin-2-yl)-methanol in 20 ml DCM was added at 50° C. and the mixture was stirred for another 15 minutes at 50° C. Triethylamine (7 ml) was then added at −50° C. and after 5 minutes the bath was removed and the mixture is naturally warmed up to 23° C. It was washed with 100 ml water and extracted with 100 ml ethyl acetate. The combined organic layers were dried over magnesium sulfate. Filter. Concentrate and flash column chromatograph using 0-15% methanol in ethyl acetate yielded 736 mg (45% yield) product.

後処理

  1. customwas removed
  2. temperaturethe mixture is naturally warmed up to 23° C
  3. washIt was washed with 100 ml water
  4. extractionextracted with 100 ml ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationFilter
  7. concentrationConcentrate

出典と根拠

ORDレコード
ord-8bfc2eee85224a60a0eac66b47602150
出典データセット
uspto-grants-2010_10
特許番号
US07812014B2

反応ノート

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