3,4-dihydro-2H-pyran → Methyl 1-((tetrahydro-2H-pyran-2-yl)oxy)cyclopropane-1-carboxylate

HRID 546119Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1([OH:8])[CH2:7][CH2:6]1)=[O:4].[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.[NH+]1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.C(OCC)C>[CH3:1][O:2][C:3]([C:5]1([O:8][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:9]2)[CH2:7][CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 25 °C

Procedure

Hydroxy-cyclopropanecarboxylic acid methyl ester (5.07 g, 43.71 mmol) was dissolved in methylene chloride (75 mL) and 3,4-dihydro-2H-pyran (3.86 g, 45.90 mmol) was added followed by pyridinium-p-toluene-sulfonic acid (1.10 g, 4.37 mmol). The reaction stirred at 25° C. for 3 h. The reaction was concentrated in vacuo to give a clear oil. The oil was dissolved in diethyl ether (75 mL), washed with saturated aqueous brine solution (25 mL), dried over sodium sulfate and concentrated in vacuo to an oil. The oil was passed through a plug of silica gel (Merck silica gel 60, 40-63 μm; 100% ethyl acetate) to afford 1-(tetrahydro-pyran-2-yloxy)-cyclopropanecarboxylic acid methyl ester (7.49 g, 86%) as a clear oil: H1-NMR (400 MHz, CDCl3) δ 1.14-1.42 (4H, m), 1.88-3.46 (6H, m), 3.46-3.54 (1H, m), 3.70-3.72 (3H, m), 3.82-3.90 (1H, m), 4.81-4.96 (1H, m).

Workup

concentrationThe reaction was concentrated in vacuo
customto give a clear oil
washwashed with saturated aqueous brine solution (25 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo to an oil

Sources & evidence

ORD record: ord-44f6f88d418d491b8e8a0ac6ac15615d
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935699B2

Reaction notes

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