Perchloric Acid → Methyl 2-(tert-butoxy)-2-(2-phenyl-1,3-thiazol-4-yl)acetate

HRID 590970ノート

反応式

HRID 590970 の反応式
Cl(O)(=O)(=O)=O.[OH:6][CH:7]([C:12]1[N:13]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:15][CH:16]=1)[C:8]([O:10][CH3:11])=[O:9]>C(OC(C)(C)C)(=O)C>[C:17]([O:6][CH:7]([C:12]1[N:13]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:15][CH:16]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:22])([CH3:18])[CH3:14]

参加物

4

反応物 2

HCID 24247Perchloric AcidHCID 70818588Methyl 2-hydroxy-2-(2-phenyl-1,3-thiazol-4-yl)acetate

生成物 1

HCID 70818322Methyl 2-(tert-butoxy)-2-(2-phenyl-1,3-thiazol-4-yl)acetate収率 83.8%

試薬・触媒・溶媒 1

HCID 10908tert-Butyl acetate溶媒

実験手順

Under a nitrogen atmosphere, perchloric acid (70%, 4 mL) was added at −10° C. to a solution of methyl 2-hydroxy-2-(2-phenyl-1,3-thiazol-4-yl)acetate (6a) (800 mg, 3.2 mmol) in terbutyl acetate (25 mL). After 1 hour, the reaction was quenched with a saturated solution of sodium bicarbonate (20 mL) and extracted with dichloromethane (2×20 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20) to afford the desired product (6b) as a white pale oil (410 mg, 1.34 mmol, 42%).

後処理

  1. customthe reaction was quenched with a saturated solution of sodium bicarbonate (20 mL)
  2. extractionextracted with dichloromethane (2×20 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20)

出典と根拠

ORDレコード
ord-9fcc35f547584d4ca6793579ec4017a8
出典データセット
uspto-grants-2016_01
特許番号
US09238026B2

反応ノート

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