Sodium borohydride → Methyl 4-hydroxytetrahydro-2H-thiopyran-3-carboxylate

HRID 1053962

반응식

HRID 1053962 반응식
[O:1]=[C:2]1[CH2:7][CH2:6][S:5][CH2:4][CH:3]1[C:8]([O:10][CH3:11])=[O:9].[BH4-].[Na+]>C1COCC1>[OH:1][CH:2]1[CH2:7][CH2:6][S:5][CH2:4][CH:3]1[C:8]([O:10][CH3:11])=[O:9]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 10374916Methyl 4-oxothiane-3-carboxylate

생성물 1

HCID 10012449Methyl 4-hydroxytetrahydro-2H-thiopyran-3-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of methyl 4-oxotetrahydro-2H-thiopyran-3-carboxylate (3.00 g, 17.2 mmol) in THF (57 mL) was stirred at 0° C. Sodium borohydride (1.30 g, 34.4 mmol) was added and the resulting mixture was stirred at ambient temperature for 4 hours. The mixture was thermally stabilized with a water bath and carefully quenched with 1N aqueous HCl. The reaction mixture was then diluted with water and extracted with EtOAc (2×). The combined organic extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford the title compound. The residue was carried forward without further purification.

후처리

  1. customThe mixture was thermally stabilized with a water bath
  2. customcarefully quenched with 1N aqueous HCl
  3. additionThe reaction mixture was then diluted with water
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic extracts were washed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-94ccdaf0f4834ef28f29f14c32a6f05c
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394282B2

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