Tetrahydrofuran → HCID 22033377, compound

HRID 1792363Notes

Reaction equation

HRID 1792363 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][O:24][CH3:25])=[CH:18][CH:17]=3)([CH3:15])[CH2:11][O:12]2)=[CH:7][CH:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:44]1[CH2:48][CH2:47][CH2:46][CH2:45]1>>[OH:44][CH2:45][CH2:46][CH2:47][CH2:48][CH:9]1[C:8]2[C:13](=[CH:14][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:6][CH:7]=2)[O:12][CH2:11][C:10]1([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][O:24][CH3:25])=[CH:20][CH:21]=1)[CH3:15]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 54259996HCID 54259996, compound

Product 1

HCID 22033377HCID 22033377, compoundYield 92.4%

Conditions

Temperature
0 °C

Procedure

(3RS,4RS)-4-[4-(t-butyl dimethylsilyloxy)-1-butyl 3-(7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methylchroman (680 mg, 1.28 mmol) was dissolved in tetrahydrofuran (10 ml), and cooled to 0° C. To this solution was added tetrabutylammonium fluoride (2.6 ml, 2.56 mmol), and the reaction mixture was stirred at room temperature for 6 hours The solvent was removed by evaporation under vacuum, and the residue was dissolved in ethyl acetate, which was washed with water. The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The product was purified by column chromatography on silica gel, eluting with 30% ethyl acetate in n-hexane to afford 487 mg of the title compound as a colorless oil. (yield: 92.4%)

Workup

  1. customwas removed by evaporation under vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwhich was washed with water
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe product was purified by column chromatography on silica gel
  8. washeluting with 30% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-2933858986d942dca62ba01a4267a183
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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