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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 566511Generated: October 31, 2026

Diethyl Ether → Dimethyl 2-(4-(diethoxymethyl)benzyl)-2-(4-(methylthio) benzyl)malonate

https://huagongshe.com/reaction/566511

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantSodium hydrideHCID 24758—
Reactant1-(Chloromethyl)-4-(methylthio)benzeneHCID 70128—
ReactantDimethyl 2-(4-(diethoxymethyl)benzyl)malonateHCID 21265723—
SolventDimethylformamideHCID 6228—
ProductDimethyl 2-(4-(diethoxymethyl)benzyl)-2-(4-(methylthio) benzyl)malonateHCID 8675623994.7%

Reaction Conditions

Temperature0 °C

Reaction Steps

To a solution of the product from Step 1 (1.42 g, 4.4 mmol) in DMF (14 mL) at 0° C. was added NaH (131 mg, 80% in mineral oil). After 1 h. 4-(methylthio)benzyl chloride (0.64 mL, 4.4 mmol) was added and the mixture was stirred a further 2 h at 0° C. Following a standard aqueous/Et2O work-up, the crude was purified by flash column (1:20 EtOAc/toluene) to give a colorless oil (1.92 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06174874B1
Source datasetuspto-grants-2001_01
ORD IDord-d319a28586c1422293aa2b9726263e87
Source noteuspto-grants-2001_01