Sodium Bicarbonate → HCID 68030291, compound

HRID 2277026Notes

Reaction equation

HRID 2277026 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[O:18][C:17](=[O:19])[C:16]([C:20](=[O:23])[CH2:21][CH3:22])=[C:15]([OH:24])[CH:14]=1)(C(C)(C)C)(C)C.C([O-])(O)=O.[Na+]>CC(O)=O.C1COCC1.O>[OH:24][C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[O:18][C:17](=[O:19])[C:16]=1[C:20](=[O:23])[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86695810HCID 86695810, compound

Product 1

HCID 68030291HCID 68030291, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

6-(4-((t-Butyldimethylsilyl)oxy)butyl)-4-hydroxy-3-propionyl-2H-pyran-2-one (XIV; 5 g; 14.1 mmol) in 150 ml AcOH/THF/water (3/1/1, v/v/v) was stirred at 28° C. for 18 h. The reaction mixture was neutralized with saturated NaHCO3, extracted with 3×150 ml EtOAc, dried with Na2SO4, and evaporated to an oil. The product was purified via silica chromatography (40% EtOAc in hexanes).

Workup

  1. extractionextracted with 3×150 ml EtOAc
  2. dry with materialdried with Na2SO4
  3. customevaporated to an oil
  4. customThe product was purified via silica chromatography (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0d945d82ff2e49349dffe07108279ff3
Source dataset
uspto-grants-2015_09
Patent number
US09133155B2

Reaction notes

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