tert-Butyl acetate → HCID 66603844、化合物

HRID 1627910ノート

反応式

HRID 1627910 の反応式
[I:1][C:2]1[C:7]([CH:8]([OH:13])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:14])[N:5]=[C:4]2[S:15][C:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:3]=12.C(O[C:26]([CH3:29])([CH3:28])[CH3:27])(=O)C.Cl(O)(=O)(=O)=O>>[I:1][C:2]1[C:7]([CH:8]([O:13][C:26]([CH3:29])([CH3:28])[CH3:27])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:14])[N:5]=[C:4]2[S:15][C:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:3]=12

参加物

4

反応物 3

HCID 10908tert-Butyl acetateHCID 24247Perchloric AcidHCID 66603698Methyl hydroxy(4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)acetate

生成物 1

HCID 66603844HCID 66603844、化合物収率 32.6%

実験手順

To a solution of methyl 2-[4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-2-hydroxyacetate (2.1 g; 5.03 mmol) in tert-butyl acetate (15 mL; 112 mmol) under a nitrogen atmosphere was added perchloric acid 70% (0.342 mL; 5.52 mmol). The reaction was stirred at room temperature for 3 days and quenched by adding a saturated solution of sodium bicarbonate. The mixture was diluted with dichloromethane and the phases were separated. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethylacetate (1-40%) in heptane furnished 0.776 g (32%) of the title compound as a solid.

後処理

  1. customquenched
  2. additionby adding a saturated solution of sodium bicarbonate
  3. additionThe mixture was diluted with dichloromethane
  4. customthe phases were separated
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash-chromatography on silica gel using a gradient of ethylacetate (1-40%) in heptane

出典と根拠

ORDレコード
ord-a9fabb154db14636a1c7894625c3781d
出典データセット
uspto-grants-2014_07
特許番号
US08785638B2

反応ノート

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