Tetrahydrofurfuryl alcohol → 2-Bromomethyl-6-(tetrahydrofuran-2-ylmethoxymethyl)pyridine

HRID 876990Notes

Reaction equation

HRID 876990 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][Br:10])[N:4]=1.[O:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][OH:17]>>[Br:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][O:17][CH2:16][CH:12]2[CH2:13][CH2:14][CH2:15][O:11]2)[N:4]=1

Participants

3

Reactant 2

HCID 7360Tetrahydrofurfuryl alcoholHCID 6036102,6-Bis(bromomethyl)pyridine

Product 1

HCID 667183702-Bromomethyl-6-(tetrahydrofuran-2-ylmethoxymethyl)pyridineYield 19%

Procedure

Prepared from 2,6-bis(bromomethyl)pyridine and (RS)-tetrahydrofuran-2-methanol by the alkylation method described for the final step of Example 32 to give the title compound (19%); NMR δH (400 MHz, CDCl3) 7.70 (1H, t, J 7.5 Hz), 7.42 (1H, d, J 7.5 Hz), 7.33 (1H, d, J 7.5 Hz), 4.73-4.65 (2H, m), 4.52 (2H, s), 4.17-4.10 (1H, m), 3.93-3.87 (1H, m), 3.82-3.77 (1H, m), 3.62-3.55 (2H, m), 2.03-1.85 (3H, m), 1.71-1.62 (1H, m); (M+H)+ 286, 288.

Sources & evidence

ORD record
ord-470ff2a328a144c8bf1fd83f1e169ffc
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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