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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1683976Generated: October 26, 2026

Diisobutylaluminum hydride → 2-[1-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl) cyclopropyl]ethanol

https://huagongshe.com/reaction/1683976

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisobutylaluminum hydrideHCID 14487—
ReactantMethyl [1-(1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl)cyclopropyl]acetateHCID 53800337—
SolventTetrahydrofuranHCID 8028—
Product2-[1-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl) cyclopropyl]ethanolHCID 5455427577%

Reaction Conditions

Temperature0 °C

Reaction Steps

To a -78° C. solution of ester from Step 7 (442 mg, 1 mmol) in 5 mL THF was added DIBAH (1.5M in toluene, 2 mL, 3 mmol), and the mixture was stirred for 2 hours with slow warming to 0° C. The reaction mixture was partitioned between 1N HCl and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and evaporated. The residue was filtered through a plug of silica gel to give 319 mg of the title compound which was used without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05639780
Source datasetuspto-grants-1997_06
ORD IDord-269b11486e864ab3bc0d1163300f15f4
Source noteuspto-grants-1997_06