6-(2-(Benzyloxy)ethoxy)hexahydrofuro[3,2-b]furan-3-yl methanesulfonate → 3-Azido-6-(2-(benzyloxy)ethoxy)hexahydrofuro[3,2-b]furan

HRID 1053925Notes

Reaction equation

CS(O[CH:6]1[CH2:10][O:9][CH:8]2[CH:11]([O:14][CH2:15][CH2:16][O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:12][O:13][CH:7]12)(=O)=O.[N:25]([Na])=[N+:26]=[N-:27]>CN(C=O)C>[N:25]([CH:6]1[CH2:10][O:9][CH:8]2[CH:11]([O:14][CH2:15][CH2:16][O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:12][O:13][CH:7]12)=[N+:26]=[N-:27]

Participants

Conditions

Temperature: 140 °C

Procedure

To a suspension of 6-(2-(benzyloxy)ethoxy)hexahydrofuro[3,2-b]furan-3-yl methanesulfonate (1.40 g, 3.91 mmol) in DMF (15 mL) was added azidosodium (1.38 g, 21.15 mmol) and the mixture was heated at 140° C. for 48 h then the mixture was filtered. The filtrate was diluted with DCM (200 mL), then washed with water (100 mL×3), followed by brine (100 mL×2). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the crude product. The crude product was used in the next reaction without further treating.

Workup

filtrationthe mixture was filtered
additionThe filtrate was diluted with DCM (200 mL)
washwashed with water (100 mL×3)
dry with materialThe organic layer was dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5f93ff7597d942449a2fd5f5d484d11b
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394281B2

Reaction notes

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