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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 916713Generated: October 25, 2026

Methyl 2-chlorobenzoate → (+)-trans-2-(2-Chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one

https://huagongshe.com/reaction/916713

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl 2-chlorobenzoateHCID 11895—
ReactantSodium hydrideHCID 24758—
Reactant(-)-trans-1-[2-Hydroxy-3-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4,6-dimethoxyphenyl]-1-ethanoneHCID 59318484—
SolventDimethylformamideHCID 6228—
Product(+)-trans-2-(2-Chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-oneHCID 59318486—

Reaction Steps

(+)-trans-1-[2-Hydroxy-3-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)- -4,6-dimethoxyphenyl]-1-ethanone (compound 13), was prepared from (+)-trans-[1-Methyl-3-(2,4,6-trimethoxy-phenyly-pyrrolidin-2-yl]-methanol using the procedures described in examples 6 & 7. Compound 13, (0.7 g, 2.2 mmol) was reacted with methyl 2-chlorobenzoate (1.15 g, 6.75 mmol) in dry DMF (15 mL) in the presence of NaH (50%, 0.54 g, 11.25 mmol), using the procedure described in example 8 to afford the title compound(4).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07271193B2
Source datasetuspto-grants-2007_09
ORD IDord-6875e4921bc2461caeddf22eba3d25b9
Source noteuspto-grants-2007_09