Tetrahydrofuran → HCID 22571559, compound

HRID 1004913Notes

Reaction equation

HRID 1004913 reaction equation
[CH3:1][C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.C1C[O:16][CH2:15][CH2:14]1.C(OCC)(=[O:20])C>C([O-])(O)=O.[Na+]>[OH:20][CH:5]1[C:6]2[C:11](=[CH:10][C:9]([C:15](=[O:16])[CH3:14])=[CH:8][CH:7]=2)[C:2]([CH3:12])([CH3:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 161371,1-Dimethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 22571559HCID 22571559, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 1-hydroxy-6-(1,3-dioxolan-2-yl)]-1,2,3,4-tetrahydro-4,4-dimethylnaphthalene (Compound D24, 54.9 mg, 0.21 mmol) in 3 ml of 10% HCa and 3 ml THF was heated at 100° C. for 1.5 h and cooled to room temperature. The reaction mixture was diluted with ethyl acetate and neutralized with sat. NaHCO3. The organic layer was further washed with brine, dried and concentrated to an oil. Purification by column chromatography (silica) with ethyl acetate/hexane (1/9) gave the title compound as a clear oil (24.8 mg).

Workup

  1. washThe organic layer was further washed with brine
  2. customdried
  3. concentrationconcentrated to an oil
  4. customPurification by column chromatography (silica) with ethyl acetate/hexane (1/9)

Sources & evidence

ORD record
ord-277e0d09cace471f9fc81129f310ae41
Source dataset
uspto-grants-2000_04
Patent number
US06051731

Reaction notes

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