Sodium hydride → HCID 54685512, compound

HRID 2277023Notes

Reaction equation

HRID 2277023 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([CH2:7]P(OC)(OC)=O)=[O:6].[OH:14][C:15]1[CH:20]=[C:19]([CH:21]([CH3:26])[CH2:22][CH2:23][CH:24]=O)[O:18][C:17](=[O:27])[C:16]=1[C:28](=[O:31])[CH2:29][CH3:30]>C1COCC1>[OH:14][C:15]1[CH:20]=[C:19]([CH:21]([CH3:26])[CH2:22][CH2:23]/[CH:24]=[CH:7]/[C:5]([O:4][CH3:3])=[O:6])[O:18][C:17](=[O:27])[C:16]=1[C:28](=[O:31])[CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 54690325HCID 54690325, compound

Product 1

HCID 54685512HCID 54685512, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

NaH (0.06 g; 1.5 mmol; 60% dispersion in mineral oil; Aldrich) was added to trimethyl phosphonoacetate (0.190 g; 1.0 mmol; Aldrich) in 10 ml THF. The reaction mixture was stirred at 25° C. for 15 min, after which 4-(4-hydroxy-2-oxo-3-propionyl-2H-pyran-6-yl)pentanal (VI; 0.124 g; 0.5 mmol) in 10 ml THF was added. The reaction mixture was stirred at 25° C. for 4 h, quenched with saturated NH4Cl, extracted with 3×20 ml EtOAc, dried with anhydrous Na2SO4, and evaporated. The product was purified via silica flash chromatography (40% EtOAc in hexanes).

Workup

  1. stirringThe reaction mixture was stirred at 25° C. for 4 h
  2. customquenched with saturated NH4Cl
  3. extractionextracted with 3×20 ml EtOAc
  4. dry with materialdried with anhydrous Na2SO4
  5. customevaporated
  6. customThe product was purified via silica flash chromatography (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-69ff9934b5f7456ea028b5dde1f0810b
Source dataset
uspto-grants-2015_09
Patent number
US09133155B2

Reaction notes

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