Oxalic Acid → HCID 71185455, compound

HRID 926415Notes

Reaction equation

[CH3:1][C:2]1([CH3:20])[CH:7]=[C:6]([CH3:8])[C:5]([CH3:10])([CH3:9])[C:4](=[CH2:11])/[C:3]/1=[C:12](/[O:15][Si](C)(C)C)\[CH:13]=[CH2:14].C(O)(=O)C(O)=O>C1(C)C=CC=CC=1.C1COCC1.O>[CH3:9][C:5]1([CH3:10])[C:6]([CH3:8])=[CH:7][C:2]([CH3:20])([CH3:1])[C:3]2[C:12](=[O:15])[CH2:13][CH2:14][CH2:11][C:4]1=2

Participants

Conditions

Temperature: 410 °C

Procedure

A solution containing (5a) (2.5 mmol) in toluene (15 ml) was injected over 1 hour through a 20 cm column packed with quartz tubes heated at 410° C. using argon as carrier. The column was washed with 5 ml of pure toluene and the collected mixture was evaporated to dryness. The concentrate was added to a solution of oxalic acid (1.12 mmol) in THF (10 ml) and water (1 ml) and the mixture was stirred at room temperature for 1 hour then quenched with a saturated bicarbonate solution and extracted with diethylether. The organic layer was washed with water and brine, then dried with MgSO4, and evaporated to dryness. The crude was purified by bulb-to-bulb distillation and column chromatography (Silicagel, Cyclohexane/EtOAc 99/1). Yield: 62%.

Workup

washThe column was washed with 5 ml of pure toluene
customthe collected mixture was evaporated to dryness
customthen quenched with a saturated bicarbonate solution
extractionextracted with diethylether
washThe organic layer was washed with water and brine
dry with materialdried with MgSO4
customevaporated to dryness
distillationThe crude was purified by bulb-to-bulb distillation and column chromatography (Silicagel, Cyclohexane/EtOAc 99/1)

Sources & evidence

ORD record: ord-dff1d129869e4dd8879337763cd7ad37
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284514B2

Reaction notes

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