Tetrahydro-2-(2-nitropropoxy)-2H-pyran synthesis
- Product Name:Tetrahydro-2-(2-nitropropoxy)-2H-pyran
- CAS Number:97945-38-5
- Molecular formula:C8H15NO4
- Molecular Weight:189.21
Yield:-
Reaction Conditions:
with toluene-4-sulfonic acid for 1 h;
Steps:
5.2.1. 2-Nitropropanol tetrahydrofuranyl and tetrahydropyranyl ether
General procedure: To 7 ml of 2-nitropropanol (8.3 g; 78.9 mmol) either 1 ml of 2,3-dihydrofurane (0.927 g; 13.07 mmol for the tetrahydrofuranyl ether) or 1 ml of 3,4-dihydro(2H) pyrane (0.93 g; 11.05 mmol, for the tetrahydropyranyl ether) was added. HPLC (75% methanol in water as the eluent on a 250 × 4.6 mm C-18 column) was run as a control. Toluenesulfonic (10 mg) acid was added as a catalyst and the reaction was monitored every 15 min by HPLC. One milliliter of portions of either 2,3-dihydrofurane (THF ether) or 3,4-dihydro-(2H)-pyrane (THP ether) were added at 10 min intervals, until the HPLC runs confirmed that the reaction was complete (after ca. 1 h and a total amount of 7 ml of 2,3-dihydrofurane or 8 ml of 3,4-dihydro-(2H)-pyrane added). Average yield: 94% of crude product, which was used without further purification.
References:
Stolze, Klaus;Rohr-Udilova, Natascha;Patel, Anjan;Rosenau, Thomas [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 2,p. 985 - 993] Location in patent:experimental part
109178-34-9
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