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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2353515Generated: October 25, 2026

4-(phenylmethoxy)-1H-indole → (4-Benzyloxy-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanone

https://huagongshe.com/reaction/2353515

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-(phenylmethoxy)-1H-indoleHCID 88465—
Reactant2,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 11041002—
ReactantHCID 178418443HCID 178418443—
CatalystZincchlorideHCID 3007855—
SolventDichloromethaneHCID 6344—
Product(4-Benzyloxy-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanoneHCID 2482377934%

Reaction Steps

A mixture of 4-benzyloxyindole (1.1 g, 4.8 mmol), ethylmagnesium bromide (1.0 M solution in THF, 5.2 mL, 5.2 mmol), zinc chloride (1.0 M solution in Et2O, 5.2 mL, 5.2 mmol) and the product of Example 1A (4.8 mmol) in 25 mL of dichloromethane was processed as described in Example 1B to provide the title compound (0.56 g, 1.6 mmol, 34% yield). MS (DCI/NH3) m/z 348 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07750039B2
Source datasetuspto-grants-2010_07
ORD IDord-8fcb911b81154f2c9bad5363202a0417
Source noteuspto-grants-2010_07