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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 654470Generated: October 30, 2026

Hydrochloric Acid → (3-Benzyl-1H-indol-1-yl)acetaldehyde

https://huagongshe.com/reaction/654470

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantMethanolHCID 887—
ReactantDiisobutylaluminum hydrideHCID 14487—
ReactantHCID 54285481HCID 54285481—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
Product(3-Benzyl-1H-indol-1-yl)acetaldehydeHCID 54560454—

Reaction Conditions

Temperature-65 °C

Reaction Steps

To a solution of the product from Step 1 (470 mg, 1.68 mmol) in toluene (15 mL) at -65° C. there was slowly added 1.0M DIBAL in toluene (2.24 mL, 2.24 mmol) and the mixture was stirred at -65° C. for 1 hour. There was slowly added MeOH (5 mL) and the mixture was then allowed to warm up to r.t. There was added H2O (20 mL) and 1N aqueous HCl (10 mL) and after shaking the organic phase was washed with H2O, dried over MgSO4 and evaporated down to an oily residue which was taken as such to the next step.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05132319
Source datasetuspto-grants-1992_07
ORD IDord-71610082909d45b593f439a4d0229de7
Source noteuspto-grants-1992_07