Hydrochloric Acid → 2-[4-(3-Hydroxypropyl)naphthyl]dioxolane

HRID 1166745노트

반응식

HRID 1166745 반응식
C([O:3][C:4]([CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]2[O:22][CH2:21][CH2:20][O:19]2)=[CH:10][CH:9]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1.O>[OH:3][CH2:4][CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]2[O:19][CH2:20][CH2:21][O:22]2)=[CH:10][CH:9]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 545306942-[4-(2-Ethoxycarbonylethyl)naphthyl]dioxolane

생성물 1

HCID 538626532-[4-(3-Hydroxypropyl)naphthyl]dioxolane수율 37.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

실험 절차

To a solution of 2-[4-(2-ethoxycarbonylethyl)naphthyl]dioxolane (210 mg, 0.70 mmol) in anhydrous THF (5 mL) was added at 0° C. 1M lithium aluminum hydride in THF (0.5 mL). THF (5 mL) was added and the mixture was stirred at room temperature for 16 hr, diluted with water (10 mL), acidified with conc. hydrochloric acid, and extracted with ether (3×10 mL). The combined organic extracts were dried (MgSO4), and concentrated. The residue was purified by flash chromatography using hexane/ethyl acetate 2:1 as eluent to provide 67 mg (37%) of a colorless oil.

후처리

  1. extractionextracted with ether (3×10 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-bc54e2d00eaf49c9ac6d1b10b491e0a4
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613942B1

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