Sodium Bicarbonate → 4-(5-Hydroxy-2-oxo-3-propionyl-2-H-pyran-6-yl)pentanol

HRID 714437Notes

Reaction equation

HRID 714437 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH:12]([C:14]1[O:19][C:18](=[O:20])[C:17]([C:21](=[O:24])[CH2:22][CH3:23])=[C:16](O)[CH:15]=1)[CH3:13])(C(C)(C)C)(C)C.C([O-])(O)=[O:27].[Na+]>CC(O)=O.C1COCC1.O>[OH:27][C:15]1[CH:16]=[C:17]([C:21](=[O:24])[CH2:22][CH3:23])[C:18](=[O:20])[O:19][C:14]=1[CH:12]([CH3:13])[CH2:11][CH2:10][CH2:9][OH:8]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 547065446-(5-(t-Butyldimethylsilyloxy)pentan-2-yl)-4-hydroxy-3-propionyl-2-H-pyran-2-one

Product 1

HCID 866958084-(5-Hydroxy-2-oxo-3-propionyl-2-H-pyran-6-yl)pentanol

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

6-(5-(t-Butyldimethylsilyloxy)pentan-2-yl)-4-hydroxy-3-propionyl-2-H-pyran-2-one (IV in Scheme 1; Example 1.3; 3 g; 8.15 mmol) in 100 ml AcOH/THF/water (3/1/1, v/v/v) was stirred for 18 h at 25° C. The reaction mixture was neutralized with saturated NaHCO3, extracted with 3×50 ml EtOAc, dried with anhydrous Na2SO4, and evaporated to an oil. The product was purified via silica chromatography (40% EtOAc in hexanes).

Workup

  1. extractionextracted with 3×50 ml EtOAc
  2. dry with materialdried with anhydrous Na2SO4
  3. customevaporated to an oil
  4. customThe product was purified via silica chromatography (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-748015cf4ee14a67895d1a17447f4bf5
Source dataset
uspto-grants-2015_11
Patent number
US09187446B2

Reaction notes

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