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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1776573Generated: November 1, 2026

Acetic Acid → HCID 86679529, compound

https://huagongshe.com/reaction/1776573

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantMorpholineHCID 8083—
ReactantSodium triacetoxyborohydrideHCID 5049666—
Reactant2-(Benzyloxy)-2-oxoethyl 4-(cyclopropylmethoxy)-3-formylbenzoateHCID 86679528—
SolventTetrahydrofuranHCID 8028—
ProductHCID 86679529HCID 86679529100%

Reaction Steps

A solution of 2-(benzyloxy)-2-oxoethyl 4-(cyclopropylmethoxy)-3-formylbenzoate (3.73 g, 10.13 mmol) and morpholine (1.15 g, 13.17 mmol) in dry THF (50 ml), under argon atmosphere, was stirred for 15 minutes at RT. Na(OAc)3BH (2.79 g, 13.17 mmol) and CH3COOH (754 μl, 13.17 mmol) were added. CH3COOH was added to reach a pH between 5 and 6. The mixture stirred at RT for 24 hours. The solvent was removed, and the crude was dissolved in EtOAc and washed with NaHCO3 sat. sol. and brine. The organic phase was dried over Na2SO4, and the solvent was removed to give 2-(benzyloxy)-2-oxoethyl 4-(cyclopropylmethoxy)-3-(morpholinomethyl)benzoate (4.45 g, quantitative yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09265768B2
Source datasetuspto-grants-2016_02
ORD IDord-8f22cf2589b74c1693b6a7780c354d28
Source noteuspto-grants-2016_02