2,2-Dimethoxypropane → HCID 86756341、化合物

HRID 567897ノート

反応式

HRID 567897 の反応式
[NH2:1][C:2]1[S:3][C:4]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].CO[C:21](OC)([CH3:23])[CH3:22].[BH4-].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.CC1C=CC(S(O)(=O)=O)=CC=1>[CH3:22][CH:21]([NH:1][C:2]1[S:3][C:4]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:23]

参加物

8

反応物 3

HCID 64952,2-DimethoxypropaneHCID 3792137ethyl 2-amino-5-benzylthiophene-3-carboxylateHCID 4311764Sodium borohydride

生成物 1

HCID 86756341HCID 86756341、化合物

試薬・触媒・溶媒 4

HCID 6101p-Toluenesulfonic acid触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

To a solution of 2-amino-5-(phenylmethyl)thiophene-3-carboxylic acid, ethyl ester (2.61 g) and 4-methylbenzenesulfonic acid (30mg) in dry toluene (50 ml) was added 2,2-dimethoxypropane. The solution was heated to reflux for 5 hours and then allowed to cool to ambient temperature. A solution of sodium borohydride (800 mg) in ethanol (100 ml) was added to the solution and the mixture was stirred at room temperature under nitrogen for 24 hours. The mixture was diluted with water and then extracted thrice with ethyl acetate. The combined organic extracts were washed with brine and then dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure to give an oil. The residue was purified by column chromatography over silica, eluting with diethyl ether:isohexane (1:19) to give the subtitle compound (550 mg).

後処理

  1. temperatureThe solution was heated
  2. temperatureto reflux for 5 hours
  3. extractionextracted thrice with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give an oil
  9. customThe residue was purified by column chromatography over silica
  10. washeluting with diethyl ether:isohexane (1:19)

出典と根拠

ORDレコード
ord-12e33d0101b04236bb0405962bdc5ff5
出典データセット
uspto-grants-2001_01
特許番号
US06180635B2

反応ノート

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