Tetrabutylammonium Fluoride → ((5S,6aR)-2,2,6a-trimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methanol

HRID 409009Notes

Reaction equation

HRID 409009 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][C@H:8]1[O:15][CH:14]2[C@:10]([CH3:18])([O:11][C:12]([CH3:17])([CH3:16])[O:13]2)[CH2:9]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[CH3:16][C:12]1([CH3:17])[O:11][C@:10]2([CH3:18])[CH2:9][C@@H:8]([CH2:7][OH:6])[O:15][CH:14]2[O:13]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66778741tert-butyldiphenyl(((5S,6aR)-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methoxy)silane

Product 1

HCID 66780018((5S,6aR)-2,2,6a-trimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methanolYield 85.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyldiphenyl(((5S,6aR)-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methoxy)silane (from step 7) (7.2 g, 0.0169 mol) in 50 mL of anhydrous THF at 0° C., TBAF (20.28 mL, 0.0203 mol) was added and stirred at room temperature for 3 h. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layers were dried over anhydrous Na2SO4, filtered and concentrated to dryness. Purified by column chromatography using hexane and ethyl ether as a gradient mixture to give 2.72 g of the title compound in 82% yield.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customPurified by column chromatography

Sources & evidence

ORD record
ord-dd35822a620c4155b960db6498327b5f
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

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