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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2428169Generated: November 1, 2026

Dichloromethane → 4-(4-Hydroxy-phenyl)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic Acid 1-tert-butyl Ester 3-methyl Ester

https://huagongshe.com/reaction/2428169

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactant4-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-5,6-dihydro-2H-pyridine-1,3-dicarboxylic Acid 1-tert-butyl Ester 3-methyl EsterHCID 67148596—
SolventTetrahydrofuranHCID 8028—
Product4-(4-Hydroxy-phenyl)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic Acid 1-tert-butyl Ester 3-methyl EsterHCID 67148247100%

Reaction Conditions

Temperature0 °C

Reaction Steps

TBAF (9.50 g, 30 mmol) was added to a sol. of compound B1 (13.4 g, 30 mmol) in THF (100 mL) at 0° C. The mixture was stirred at 0° C. for 1 h. CH2Cl2 was added, and the mixture was washed with aq. sat. NH4Cl, water, and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (10.0 g, quantitative yield) that was used further without purification. LC-MS: tR=0.92 min; ES+: 334.23.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07968720B2
Source datasetuspto-grants-2011_06
ORD IDord-e85fe98e795040f4998b7deebb97cec8
Source noteuspto-grants-2011_06