1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-[Azido-(5-methylfuran-2-yl)methyl]tetrahydropyran

HRID 1482455Notes

Reaction equation

C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:18][C:19]1[O:23][C:22]([CH:24]([CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)O)=[CH:21][CH:20]=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:15]([CH:24]([C:22]1[O:23][C:19]([CH3:18])=[CH:20][CH:21]=1)[CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[N+:16]=[N-:17]

Participants

Conditions

Temperature: 0 °C

Procedure

6.08 g (22 mmol, 1.1 eq) of diphenylphosphoryl azide were added dropwise to a solution of 4.43 g (20 mmol, 1 eq) of (5-methylfuran-2-yl)-(tetrahydropyran-4-yl)methanol at 89% in 60 ml of toluene. The reaction medium was cooled to 0° C. and then 3.3 ml (22 mmol, 1.1 eq) of 1,8-diazabicyclo[5.4.0]undec-7-ene were added dropwise. The reaction medium was stirred at ambient temperature for 22 hours. The reaction medium was separated by settling out and the organic phase was washed with water and then with 1 N hydrochloric acid, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed on silica gel (column Analogix SF40-240 g, Spot II) eluted with heptane/ethyl acetate (95/5). 3.09 g of 4-[azido-(5-methylfuran-2-yl)methyl]tetrahydropyran were obtained. Yield=70%.

Workup

customThe reaction medium was separated
washthe organic phase was washed with water
dry with materialwith 1 N hydrochloric acid, dried over magnesium sulfate
filtrationfiltered
customevaporated
customThe residue was chromatographed on silica gel (column Analogix SF40-240 g, Spot II)
washeluted with heptane/ethyl acetate (95/5)

Sources & evidence

ORD record: ord-64e5f9ccbd244bdfbb96236c1484b45a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09415039B2

Reaction notes

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