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Ethyl Acetate → HCID 45092074、化合物

HRID 525351
ノート
印刷プレビュー

反応式

HRID 525351 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])C)C(O)(C)C.CC(C)([O-])C.[K+].CCOC(C)=O>C1COCC1.CCCCCC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:16]([CH3:18])([CH3:19])[O:15][C:14](=[O:20])[NH:13]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 89827431HCID 89827431、化合物

生成物 1

HCID 45092074HCID 45092074、化合物収率 98.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

To a solution of tert-butyl (1-(2-fluorophenyl)-2-hydroxy-2-methylpropyl)carbamate (400 mg, 1.41 mmol) in THF (8 mL) was added potassium tert-butoxide (316.87 mg, 2.82 mmol) at 0-5° C. The resulting reaction mixture was stirred for 2 hours at ambient temperature. After completion of the reaction (monitored by TLC, TLC system: 50% EtOAc in hexane), the reaction mixture was quenched with ice water and extracted with EtOAc. The combined organic layers were washed with, water, saturated NaCl solution and dried on Na2SO4, filtered, and concentrated under reduced pressure to afford 4-(2-fluorophenyl)-5,5-dimethyloxazolidin-2-one (290 mg, 98.18%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.05 (s, 1H), 7.44-7.35 (m, 2H), 7.30-7.22 (m, 2H), 4.88 (s, 1H), 1.53 (s, 3H), 0.88 (s, 3H). m/z (ESI) 210.1 (M+H)+.

後処理

  1. customThe resulting reaction mixture
  2. customthe reaction mixture was quenched with ice water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with, water, saturated NaCl solution
  5. customdried on Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-e103b8d826e64ec78f57be63b2010e06
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09340549B2

反応ノート

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