Water → HCID 89525595, compound

HRID 1050972Notes

Reaction equation

C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2.[CH3:29][C:30]1[O:34][C:33]([CH:35]([CH:37]2[CH2:41][CH2:40][CH2:39][S:38]2)O)=[CH:32][CH:31]=1.O>C1(C)C=CC=CC=1>[N:15]([CH:35]([CH:37]1[CH2:41][CH2:40][CH2:39][S:38]1)[C:33]1[O:34][C:30]([CH3:29])=[CH:31][CH:32]=1)=[N+:16]=[N-:17]

Participants

Conditions

Temperature: 0 °C

Procedure

39.3 ml (0.18 mol; 1.2 eq) of diphenylphosphoryl azide and then 27.3 ml (0.18 mol; 1.2 eq) of 1,8-diazabicyclo[5.4.0]undec-7-ene were added dropwise to a solution of 30.21 g (0.15 mol; 1.0 eq) of (5-methylfuran-2-yl)-(tetrahydrothiophen-2-yl)methanol in 350 ml of toluene cooled to 0° C. The mixture was allowed to return to ambient temperature gently and was then stirred for 2 days. The reaction medium was treated with water and extracted with ethyl acetate. The organic phases were combined, washed with a 1 M sodium hydrogen phosphate solution, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed on silica gel (column puriFlash IR-50SI/800G, puriFlash) eluted with heptane/ethyl acetate (95/5). 26.95 g of 2-[azido-(tetrahydrothiophen-2-yl)methyl]-5-methylfuran were obtained (mixture of the 2 diastereoisomers). Yield=79%.

Workup

customto return to ambient temperature
extractionextracted with ethyl acetate
washwashed with a 1 M sodium hydrogen phosphate solution
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customThe residue was chromatographed on silica gel (column puriFlash IR-50SI/800G, puriFlash)
washeluted with heptane/ethyl acetate (95/5)

Sources & evidence

ORD record: ord-b8cec7dd71be40eeae0729173a2e22ae
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388149B2

Reaction notes

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