tert-Butyl acetate → Methyl 2-[4-chloro-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-2-tert-butoxyacetate

HRID 1627894Notes

Reaction equation

HRID 1627894 reaction equation
[Cl: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>>[Cl: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

Participants

4

Reactant 3

HCID 10908tert-Butyl acetateHCID 24247Perchloric AcidHCID 66603831Methyl 2-[4-chloro-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-2-hydroxyacetate

Product 1

HCID 66603984Methyl 2-[4-chloro-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-2-tert-butoxyacetateYield 59%

Procedure

To a solution of methyl 2-[4-chloro-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-2-hydroxyacetate (0.100 g, 0.307 mmol) in tert-butyl acetate (1.5 mL; 11.23 mmol) under a nitrogen atmosphere was added perchloric acid 70% (0.029 mL; 0.338 mmol). The reaction was stirred at room temperature for 5 h 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 (5-40%) in heptane furnished 0.069 g (59%) of the title compound as a solid.

Workup

  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 (5-40%) in heptane

Sources & evidence

ORD record
ord-2247d2081bd040d8ba8dc5c104dd6560
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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