Sodium hydride → Methyl 2-(2-thienylmethoxy)acetate

HRID 128655

반응식

HRID 128655 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][OH:7].[H-].[Na+].Br[CH2:11][C:12]([O:14][CH3:15])=[O:13]>C1COCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][O:7][CH2:11][C:12]([O:14][CH3:15])=[O:13]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 694672-Thiophenemethanol

생성물 1

HCID 23369384Methyl 2-(2-thienylmethoxy)acetate수율 49%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirring 25 mL solution of 1.14 g (10 mmol) of thiophenemethanol in THF was added 0.24 g (10 mmol) of NaH. After the evolution of gas had ceased, 1.53 g (10 mmol) of methyl bromoacetate was added to the reaction. After 15 minutes, the reaction mixture was filtered. The solvent was removed under reduced pressure. The residue was then dissolved in 50 mL of EtOAc. The organic layer was washed with 3×50 mL of H2O, and was treated in the manner described above in Example 7. The residue was chromatographed to yield 0.91 g (49%) of product. Analysis calculated for C8H10O3S (M.W. 186.23): C, 51.60; H, 5.41. Found: C, 51.41; H, 5.60.

후처리

  1. filtrationthe reaction mixture was filtered
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was then dissolved in 50 mL of EtOAc
  4. washThe organic layer was washed with 3×50 mL of H2O
  5. additionwas treated in the manner
  6. customThe residue was chromatographed

출처 및 근거

ORD 기록
ord-ea04292fede442ef90d7ec61558bad7a
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464830

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