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ChemicalBook CAS DataBase List 5-(Azidomethyl)-3,3-difluorodihydro-2(3H)-Furanone
189136-13-8

5-(Azidomethyl)-3,3-difluorodihydro-2(3H)-Furanone synthesis

2synthesis methods
3,3-difluoro-5-(iodomethyl)oxolan-2-one

1256080-97-3
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5-(Azidomethyl)-3,3-difluorodihydro-2(3H)-Furanone

189136-13-8
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Yield:-

Reaction Conditions:

with sodium azide in dimethyl sulfoxide at 25; for 12 h;

Steps:

76.2 Step 2: 5-(azidomethyl)-3,3-difluorodihydrofuran-2(3H)-one

To a solution of 3,3-difluoro-5-(iodomethyl)tetrahydrofuran-2-one (2 g, 7.63 mmol) in DMSO (20 mL) was added azidosodium (596 mg, 9.16 mmol) at 25 °C. The reaction mixture was stirred for 12 hrs at 25 °C. The reaction mixture was quenched with water (30 mL) and extracted with EtOAc (60 mL). The organic layer was separated and washed with brine (20 mL), dried over Na2SC>4, filtered and then the filtrate was concentrated under reduced pressure to give the title compound (1.2 g, 89% yield) as a yellow oil, which was used in the next step without purification. NMR (400 MHz, CDCb) d = 4.78 - 4.74 (m, 1H), 3.76 - 3.72 (m, 1H), 3.58- 3.53 (m, 1H), 2.84 - 2.71 (m, 1H), 2.68 - 2.54 (m, 1H).

References:

WO2021/154842,2021,A1 Location in patent:Paragraph 0822; 0826-0828