Thiazole → Tert-butyl 4-hydroxy-4-(1,3-thiazol-2-yl)cyclohexanecarboxylate

HRID 410440ノート

反応式

HRID 410440 の反応式
C([Mg]Cl)(C)C.[Cl-].[Li+].[S:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.[O:13]=[C:14]1[CH2:19][CH2:18][CH:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1>C1COCC1>[OH:13][C:14]1([C:9]2[S:8][CH:12]=[CH:11][N:10]=2)[CH2:15][CH2:16][CH:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]1

参加物

5

反応物 3

HCID 9256ThiazoleHCID 14940589tert-Butyl 4-oxocyclohexane-1-carboxylateHCID 178461733HCID 178461733、化合物

生成物 1

HCID 67257275Tert-butyl 4-hydroxy-4-(1,3-thiazol-2-yl)cyclohexanecarboxylate収率 80.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a flask containing THF (82 mL) was added isopropylmagnesium chloride/lithium chloride (1.2 M in THF, 37.7 mL, 45 mmol). A solution of thiazole (3.5 g, 41 mmol) in THF (20 mL) was added slowly. The reaction was stirred for one hour. A solution of tert-butyl 4-oxocyclohexanecarboxylate (12.23 g, 62 mmol) in THF (20 mL) was added and the reaction was stirred for 3 hours. The reaction was then quenched slowly with saturated ammonium chloride and diluted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated. Flash chromatography was used for purification to yield tert-butyl 4-hydroxy-4-(1,3-thiazol-2-yl)cyclohexanecarboxylate (9.25 g, 33 mmol, 79% yield). MS ESI: [M+H]+ m/z 284.1.

後処理

  1. stirringthe reaction was stirred for 3 hours
  2. customThe reaction was then quenched slowly with saturated ammonium chloride
  3. additiondiluted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customFlash chromatography was used for purification

出典と根拠

ORDレコード
ord-3efb611faba1468a8551c0fdb7d85fc4
出典データセット
uspto-grants-2014_06
特許番号
US08759366B2

反応ノート

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