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Perchloric Acid → Methyl 2-{1-bromothieno[3,2-f]quinolin-2-yl}-2-(tert-butoxy)acetate

HRID 591018
ノート
印刷プレビュー

反応式

HRID 591018 の反応式
[Br:1][C:2]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[S:4][C:3]=1[CH:15]([OH:20])[C:16]([O:18][CH3:19])=[O:17])[N:11]=[CH:10][CH:9]=[CH:8]3.Cl(O)(=O)(=O)=O.C(=O)(O)[O-].[Na+]>C(OC(=O)C)(C)(C)C>[Br:1][C:2]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[S:4][C:3]=1[CH:15]([O:20][C:6]([CH3:7])([CH3:2])[CH3:5])[C:16]([O:18][CH3:19])=[O:17])[N:11]=[CH:10][CH:9]=[CH:8]3
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24247Perchloric AcidHCID 516892Sodium BicarbonateHCID 86717835Methyl 2-{1-bromothieno[3,2-f]quinolin-2-yl}-2-hydroxyacetate

生成物 1

HCID 86717834Methyl 2-{1-bromothieno[3,2-f]quinolin-2-yl}-2-(tert-butoxy)acetate収率 60.5%

試薬・触媒・溶媒 1

HCID 10908tert-Butyl acetate溶媒

反応条件

温度
-5 °C

実験手順

To a suspension of methyl 2-{1-bromothieno[3,2-f]quinolin-2-yl}-2-hydroxyacetate (16h) (152 mg, 0.43 mmol) in tert-butylacetate (2.3 mL) at −10° C. was added perchloric acid (69.4 μL). The mixture was stirred at −5° C. for 5 hours and then warmed at room temperature for 1 hour more. The mixture was then basified with a saturated aqueous solution of sodium bicarbonate until pH 8. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by 2 preparative TLC (cyclohexane/ethyl acetate 60/40) to afford the desired product (16i) (55 mg, 0.13 mmol, 31%) as beige powder.

後処理

  1. temperaturewarmed at room temperature for 1 hour more
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by 2 preparative TLC (cyclohexane/ethyl acetate 60/40)

出典と根拠

ORDレコード
ord-28555d43918f4061aaf848a17db85192
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238026B2

反応ノート

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