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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 920113Generated: October 29, 2026

Tetrabutylammonium Fluoride → ethyl (1S,1aS,6bR)-5-hydroxy-1a,6b-dihydro-1H-cyclopropa[b]benzofuran-1-carboxylate

https://huagongshe.com/reaction/920113

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactant(1S,1aS,6bR)-Ethyl-5-((tert-butyldimethylsilyl)oxy)-1a,6b-dihydro-1H-cyclopropa[b]benzofuran-1-carboxylateHCID 131734886—
SolventTetrahydrofuranHCID 8028—
Productethyl (1S,1aS,6bR)-5-hydroxy-1a,6b-dihydro-1H-cyclopropa[b]benzofuran-1-carboxylateHCID 8967023557%

Reaction Steps

Tetra-n-butylammonium fluoride (TBAF, 1M in THF, 4 mmol) was added dropwise to a solution of the product of Step A (7.3 g, crude) in THF (100 mL) at 0° C. The reaction was stirred at RT for 30 min. The mixture was concentrated and purified by column chromatography to afford the title compound as a solid (2.52 g, 57% for 2 steps, 72% ee).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09273046B2
Source datasetuspto-grants-2016_03
ORD IDord-a5a525f98fb04440b06e8e4a11ea08db
Source noteuspto-grants-2016_03