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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1190977Generated: October 30, 2026

Hydrochloric Acid → HCID 58495545, compound

https://huagongshe.com/reaction/1190977

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantMethanolHCID 887—
Reactant(Dimethyl sulfide)trihydroboronHCID 12423031—
ReactantHCID 58495633HCID 58495633—
SolventTetrahydrofuranHCID 8028—
ProductHCID 58495545HCID 5849554536%

Reaction Steps

Under a nitrogen atmosphere, add borane-dimethylsulfide complex (20.3 mL, 40.6 mmol, 2M solution in THF) to a solution of 5-cyclohexyloxy-pyridine-2-carbonitrile (0.82 g, 4.06 mmol) in THF (800 mL) at 0° C. Warm the mixture to room temperature and stir overnight. Cool the mixture in an ice-bath, add methanol (15 mL) and concentrated HCl (2 mL). Stir for 2 h, and concentrate in vacuo. Dissolve the residue in saturated aqueous K2CO3. Extract with DCM and wash the organic phase with water and brine. Dry the organic phase over Na2SO4, filter, and concentrate in vacuo to obtain the title compound (0.3 g, 36%). MS (ES+) m/z: 207 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08680091B2
Source datasetuspto-grants-2014_03
ORD IDord-6bfa34e64c524aaaa7b61a50f8df82a4
Source noteuspto-grants-2014_03