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

HRID 1166745Notes

Reaction equation

HRID 1166745 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bc54e2d00eaf49c9ac6d1b10b491e0a4
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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