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

HRID 1039931ノート

反応式

HRID 1039931 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2 回

実験手順

To a flask containing TI-IF (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. additionTo a flask containing TI-IF (82 mL)
  2. stirringthe reaction was stirred for 3 hours
  3. customThe reaction was then quenched slowly with saturated ammonium chloride
  4. additiondiluted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customFlash chromatography was used for purification

出典と根拠

ORDレコード
ord-678db9765ee340d4b0dc414f859646d3
出典データセット
uspto-grants-2013_10
特許番号
US08551984B2

反応ノート

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