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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1035240Generated: October 31, 2026

4-Hydroxybenzaldehyde → HCID 58043115, compound

https://huagongshe.com/reaction/1035240

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-HydroxybenzaldehydeHCID 126—
ReactantWaterHCID 962—
ReactantCesium carbonateHCID 10796—
Reactant1-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonateHCID 58043099—
SolventDimethylacetamideHCID 31374—
ProductHCID 58043115HCID 5804311566.1%

Reaction Conditions

Temperature110 °C

Reaction Steps

Intermediate 53B (5.0 g, 15.5 mmol) was dissolved in DMA (40 mL) and 4-hydroxybenzaldehyde (2.17 g, 17.8 mmol) was added followed by Cs2CO3 (5.8 g, 17.8 mmol). The mixture was stirred at 110° C. for 5 h. Water was added and the mixture was extracted trice with DCM. The solution was filtered through a phase separator and the solvent was removed by evaporation. Ether was added to the residue and the formed solid was filtered and washed with ether. The product was dried in vacuo to give 3.58 g (66%) of 71A as a beige solid. 1H NMR (500 MHz, CDCl3): δ 4.37 (m, 1H), 4.70 (m, 1H), 4.79 (m, 1H), 5.18 (m, 2H), 6.91 (d, 2H), 7.53 (t, 2H), 7.60 (t, 1H), 7.87 (d, 2H), 8.16 (d, 2H), 9.92 (s, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08546375B2
Source datasetuspto-grants-2013_10
ORD IDord-d57330169b324064a880f5c671d19ecc
Source noteuspto-grants-2013_10