Water → HCID 89525341, compound

HRID 1050983Notes

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]([C@@H:35]([CH:37]2[CH2:41][CH2:40][CH2:39][O:38]2)O)=[CH:32][CH:31]=1.O>C1(C)C=CC=CC=1>[N:15]([C@H:35]([CH:37]1[CH2:41][CH2:40][CH2:39][O: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

11.9 ml (55.3 mmol; 1.2 eq) of diphenylphosphoryl azide and then 8.3 ml (55.3 mmol; 1.2 eq) of 1,8-diazabicyclo[5.4.0]undec-7-ene were added dropwise to a solution of 8.40 g (46.1 mmol; 1.0 eq) of (5-methylfuran-2-yl)-(R)-tetrahydrofuran-2-ylmethanol in 300 ml of toluene cooled to 0° C. The mixture was allowed to return to ambient temperature gently and was then stirred for 24 hours. The reaction medium was treated with water and extracted with ethyl acetate, The organic phases were combined, washed with a 1 M sodium dihydrogen phosphate solution, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed on silica gel (column puriFlash IR-50SI/300G, puriFlash) eluted with heptane/ethyl acetate (90/10). 6.0 g of 2-((R)-azidotetrahydrofuran-2-ylmethyl)-5-methylfuran were obtained (mixture of the 2 diastereoisomers). Yield=63%.

Workup

customto return to ambient temperature
extractionextracted with ethyl acetate
washwashed with a 1 M sodium dihydrogen phosphate solution
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customThe residue was chromatographed on silica gel (column puriFlash IR-50SI/300G, puriFlash)
washeluted with heptane/ethyl acetate (90/10)

Sources & evidence

ORD record: ord-2ffab6153e8e4dd8a1d00aab0440fca4
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388149B2

Reaction notes

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