Ethyl Glycolate → HCID 54695711, compound

HRID 1984290Notes

Reaction equation

[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][OH:3].[H-].[Na+].Cl[C:11]1[C:16]([C:17](OCC)=[O:18])=[CH:15][N:14]=[CH:13][CH:12]=1>COCCOC>[OH:18][C:17]1[C:16]2[CH:15]=[N:14][CH:13]=[CH:12][C:11]=2[O:3][C:2]=1[C:1]([O:5][CH2:6][CH3:7])=[O:4]

Participants

Conditions

Temperature: 70 °C

Procedure

Ethyl glycolate (7.26 g, 59.7 mmol) was added slowly into a suspension of sodium hydride (2.95 g of 60% dispersion in mineral oil, 73.8 mmol) in 85 mL of 1,2-dimethoxyethane (DME) at 0° C., and the mixture was stirred for another 30 min. A solution of ethyl 4-chloronicotinate (6.20 g, 33.4 mmol) in 20 mL of DME was added slowly into the reaction mixture at room temperature. The mixture was heated to 70° C. and maintained at that temperature overnight. The solvent was evaporated and the residue was dissolved in 100 mL of water, and washed with hexane 3 times. The pH of the water solution was adjusted to about 5 using acetic acid to pH 5, and a yellow precipitate was formed. The yellow precipitate was filtered, washed with a small amount of water (20 mL×3), and dried overnight in vacuo to give ethyl 3-hydroxyfuro[3,2-c]pyridine-2-carboxylate free base as a yellow solid (5.79 g) which was used for the next step without further purification.

Workup

temperaturemaintained at that temperature overnight
customThe solvent was evaporated
dissolutionthe residue was dissolved in 100 mL of water
washwashed with hexane 3 times
customa yellow precipitate was formed
filtrationThe yellow precipitate was filtered
washwashed with a small amount of water (20 mL×3)
customdried overnight in vacuo

Sources & evidence

ORD record: ord-ce6139ccedc9403abc9b4dce36cc1468
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544693B2

Reaction notes

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