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Sodium borohydride → (3-(2-(Benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazol-5-yl) methanol

HRID 453120
ノート
印刷プレビュー

反応式

HRID 453120 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:20]=[C:19]([C:21](OCC)=[O:22])[S:18][N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CCO>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:20]=[C:19]([CH2:21][OH:22])[S:18][N:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 59549530Ethyl 3-(2-(benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazole-5-carboxylate

生成物 1

HCID 59549526(3-(2-(Benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazol-5-yl) methanol収率 88%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of ethyl 3-(2-(benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazole-5-carboxylate (0.45 g, 1.20 mmol) in EtOH (25 ml) was added sodium borohydride (0.113 g, 3.0 mmol) portion wise. 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 2 ml of water and concentrated under vacuum. Added water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum to get the desired product (0.35 g, 88%) that was carried forward to the next step without further purification.

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 2 ml of water
  5. concentrationconcentrated under vacuum
  6. extractionAdded water (50 ml) and extracted with ethyl acetate (3×50 ml)
  7. dry with materialThe combined organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-519cdc53457d421b8a171c54ab7687a8
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08492414B2

反応ノート

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