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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2389084Generated: October 30, 2026

Tetrahydrofuran → HCID 67413948, compound

https://huagongshe.com/reaction/2389084

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantTriphenylphosphineHCID 11776—
ReactantDiisopropyl diazene-1,2-dicarboxylateHCID 75555—
ReactantHCID 15767265HCID 15767265—
Reactant(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-oneHCID 51066623—
ProductHCID 67413948HCID 6741394827%

Reaction Steps

The compound was prepared in a manner similar as to that described above using (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one, 4-cyclopentyl-cyclohexanol (1.5 g, 0.0090 mol), triphenylphosphine (2.6 g, 0.0099 mol), tetrahydrofuran (45 mL, 0.55 mol) and diisopropyl azodicarboxylate (2.0 g, 0.0099 mol) to give 895 mg of a 1.6 to 1 diasteromeric ratio of the desired compound as a yellow solid (27%). ESI-MS: 368 (M+H)+. 1H NMR (400 MHz, CDCl3) δ=7.80-7.63 (m, 3 H), 7.39 (dd, J=1.9, 8.7 Hz, 1 H), 7.22-7.08 (m, 2 H), 4.70-4.58 (br. s., 0.63 H), 4.43-4.36 (s, 2 H), 4.34-4.21 (tt, J=4.2, 6.5 Hz, 0.39 H), 2.04 (s, 2 H), 1.87-1.70 (m, 2 H), 1.65-0.77 (m, 17 H)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08269043B2
Source datasetuspto-grants-2012_09
ORD IDord-78dc969e3d3f47b68768c18ea418d281
Source noteuspto-grants-2012_09