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

HRID 714438Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:15](=[O:18])[CH2:16][CH3:17])[C:5](=[O:14])[O:6][C:7]=1[CH:8]([CH3:13])[CH2:9][CH2:10][CH2:11][OH:12].[Na].C([O-])(O)=O.[Na+]>ClCCl.N1C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]([C:15](=[O:18])[CH2:16][CH3:17])[C:5](=[O:14])[O:6][C:7]=1[CH:8]([CH3:13])[CH2:9][CH2:10][CH:11]=[O:12]

Participants

Conditions

Temperature: 25 °C

Procedure

4-(5-Hydroxy-2-oxo-3-propionyl-2-H-pyran-6-yl)pentanol (V in Scheme 1; Example 1.4; 0.38 g; 1.5 mmol; Aldrich) was dissolved in 20 ml dichloromethane and 0.6 ml pyridine. Sodium periodinate (0.7 g; 1.65 mmol; Aldrich) was added and stirred for 2 h at 25° C., after which reaction mixture was neutralized with saturated NaHCO3 and extracted with 3×20 ml CH2Cl2. The pooled organic extracts were dried with anhydrous Na2SO4, evaporated, and purified via silica chromatography (20% EtOAc in hexanes).

Workup

customafter which reaction mixture
extractionextracted with 3×20 ml CH2Cl2
dry with materialThe pooled organic extracts were dried with anhydrous Na2SO4
customevaporated
custompurified via silica chromatography (20% EtOAc in hexanes)

Sources & evidence

ORD record: ord-dfe9398952cc4de2828572291ea07cf9
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187446B2

Reaction notes

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