Sodium borohydride → [3-(4-Benzyloxyphenyl)-[1,2,4]thiadiazol-5-yl]-methanol

HRID 453106

反応式

HRID 453106 の反応式
C([O:3][C:4]([C:6]1[S:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[N:7]=1)=O)C.[BH4-].[Na+]>CCO>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[N:7]=[C:6]([CH2:4][OH:3])[S:10][N:9]=2)=[CH:12][CH:13]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 595495323-(4-Benzyloxyphenyl)-[1,2,4]thiadiazole-5-carboxylic acid ethyl ester

生成物 1

HCID 59549522[3-(4-Benzyloxyphenyl)-[1,2,4]thiadiazol-5-yl]-methanol収率 30%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 3-(4-benzyloxyphenyl)-[1,2,4]thiadiazole-5-carboxylic acid ethyl ester (0.20 g, 0.59 mmol) in EtOH (20 ml) was added sodium borohydride (0.44 g, 1.17 mmol) portion wise and the resulting reaction mixture was stirred at room temperature for 2 h. After the completion of the reaction (TLC monitoring), the reaction mass was cooled to 0° C., quenched it with 5 ml of water and concentrated under vacuum. Added 75 ml water and extracted with ethyl acetate (3×30 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified over silica gel (100-200 M, 30% EtOAc-Hexane) to get the desired product (0.052 g, 30%).

後処理

  1. customthe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring)
  3. temperaturethe reaction mass was cooled to 0° C.
  4. customquenched it with 5 ml of water
  5. concentrationconcentrated under vacuum
  6. additionAdded 75 ml water
  7. extractionextracted with ethyl acetate (3×30 ml)
  8. dry with materialThe combined organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customThe crude residue was purified over silica gel (100-200 M, 30% EtOAc-Hexane)

出典と根拠

ORDレコード
ord-903234933b774e1e8e71b928d59b05de
出典データセット
uspto-grants-2013_07
特許番号
US08492414B2

関連ノート

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