Sodium Azide → 2-(2-(2-Azidoethoxy)ethoxy)ethanol

HRID 1844290Notes

Reaction equation

Cl[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10].[N-:11]=[N+:12]=[N-:13].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[N:11]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10])=[N+:12]=[N-:13]

Participants

Conditions

Temperature: 120 °C

Procedure

In a 250 mL flask, 2-[2-(2-chloroethoxy)ethoxy]ethanol (1) (6000 mg, 35.7 mmol), NaN3 (6964 mg, 107 mmol) and tetrabutylammonium iodide (TBAI) (656 mg, 1.7 mmol) were added to 80 mL DMF. The temperature was slowly raised to 120° C. and the reaction mixture was stirred under argon overnight. The solvent was evaporated and the residue was purified by FCC to afford 2 as slightly yellow oil (4150 mg, 66%). 1H NMR (400 MHz, CDCl3): δ 3.29 (t, J=5.2 Hz, 2H), 3.50 (m, 2H), 3.57-3.64 (m, 8H). 13C NMR (100 MHz, CDCl3): δ 50.59, 61.60, 69.98, 70.34, 70.59, 72.56.

Workup

customThe solvent was evaporated
customthe residue was purified by FCC

Sources & evidence

ORD record: ord-957944c61532438bbe613b5dc30399ed
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946391B2

Reaction notes

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