Water → HCID 54142683, compound

HRID 1490135Notes

Reaction equation

HRID 1490135 reaction equation
[Si]([O:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[O:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH:15]1[O:14][C@H:11]1[CH2:12][CH2:13][C@@H:9]([OH:8])[CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 53875127HCID 53875127, compound

Product 1

HCID 54142683HCID 54142683, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of (1R,3S)-1-(tert-butyldimethylsilyl)oxy-3-tetrahydropyranyloxycyclopentane (11.3 g, 33.0 mmol) in dry THF (40 ml) was added a 1.0M solution of tetrabutylammonium fluoride in THF (50 ml, 50.0 mmol). After stirring for 1 h at room temperature, the reaction mixture was poured into water (200 ml) and the whole extracted with ether (200 ml). The ether phase was washed with brine (200 ml), dried (MgSO4) and concentrated under reduced pressure. Chromatographic purification of the residue {SiO2, 800 g; hexane/ethyl acetate (2:1) with 1% of triethylamine} provided 5.47 g (73%) of the title compound as a colorless oil: 1H NMR δ4.73-4.64 (m, 1H), 4.42-4.23 (m, 2H), 3.95-3.81 (m, 1H), 3.59-3.44 (m, 1H), 2.20-1.20 (m, 13H).

Workup

  1. extractionthe whole extracted with ether (200 ml)
  2. washThe ether phase was washed with brine (200 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customChromatographic purification of the residue {SiO2, 800 g

Sources & evidence

ORD record
ord-2ec3e4429d954aa69171def91aa7c8b9
Source dataset
uspto-grants-1997_10
Patent number
US05681858

Reaction notes

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