tert-Butyl acetate → Methyl 2-(tert-butoxy)-2-(2-methyl-1,3-thiazol-4-yl)acetate

HRID 591011Notes

Reaction equation

HRID 591011 reaction equation
Cl(O)(=O)(=O)=O.[OH:6][CH:7]([C:12]1[N:13]=[C:14]([CH3:17])[S:15][CH:16]=1)[C:8]([O:10][CH3:11])=[O:9].C(O[C:22]([CH3:25])([CH3:24])[CH3:23])(=O)C>>[C:22]([O:6][CH:7]([C:12]1[N:13]=[C:14]([CH3:17])[S:15][CH:16]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 3

HCID 10908tert-Butyl acetateHCID 24247Perchloric AcidHCID 86717830Methyl 2-hydroxy-2-(2-methyl-1,3-thiazol-4-yl)acetate

Product 1

HCID 70819407Methyl 2-(tert-butoxy)-2-(2-methyl-1,3-thiazol-4-yl)acetateYield 21%

Procedure

Under a nitrogen atmosphere, perchloric acid (70%, 3.75 mL) was added at −10° C. to a solution of methyl 2-hydroxy-2-(2-methyl-1,3-thiazol-4-yl)acetate (15b) (590 mg, 3.15 mmol) in tertbutyl acetate (25 mL). After 1 hour, the reaction was quenched with a saturated aqueous solution of sodium carbonate 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 (dichloromethane/ethyl acetate 75/25) to afford the desired product (15c) as a white solid (160 mg, 0.66 mmol, 21%).

Workup

  1. customthe reaction was quenched with a saturated aqueous solution of sodium carbonate
  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 (dichloromethane/ethyl acetate 75/25)

Sources & evidence

ORD record
ord-a0155373042d468ebceb1c08439e8652
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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