Hydrofluoric Acid → HCID 15838326, compound

HRID 1938919Notes

Reaction equation

HRID 1938919 reaction equation
[C:1]([N:9]1[C:26](=[O:27])[CH2:25][CH2:24][C@@:23]2([CH3:28])[C:10]1=[CH:11][CH2:12][C@@H:13]1[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]1[CH2:15][CH2:16][C@@H:17]2[O:29][Si](C(C)(C)C)(C)C)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F.C(=O)(O)[O-].[Na+]>C1COCC1>[C:1]([N:9]1[C:26](=[O:27])[CH2:25][CH2:24][C@@:23]2([CH3:28])[C:10]1=[CH:11][CH2:12][C@@H:13]1[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]1[CH2:15][CH2:16][C@@H:17]2[OH:29])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 15838325HCID 15838325, compoundHCID 178435160HCID 178435160, compound

Product 1

HCID 15838326HCID 15838326, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the product of Step A, above, (2.0 g) in THF (80 ml) in a polyethylene bottle was added hydrofluoric acid (2.0 ml) dropwise. The mixture was stirred at room temperature until the reaction was complete. The mixture was neutralized with saturated sodium bicarbonate solution until slightly alkaline. The mixture was concentrated, and extracted with methylene chloride. The organic layer was dried (Na2SO4), and concentrated to a residue which was purified via flash silica gel column chromatography eluted with 40-50% EtOAc in hexane to give the title product.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated to a residue which
  5. customwas purified via flash silica gel column chromatography
  6. washeluted with 40-50% EtOAc in hexane

Sources & evidence

ORD record
ord-7e2a7387bc9446639ca32919826dab69
Source dataset
uspto-grants-1997_12
Patent number
US05693809

Reaction notes

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