Tetrahydrofuran → 1-(1-Benzyloxymethylimidazol-2-yl)-2-methyl-1-propanol

HRID 3143Notes

Reaction equation

[CH2:1]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]1C[O:18][CH2:17][CH2:16]1.[Li][CH2:21]CCC>O>[CH2:1]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[CH:17]([OH:18])[CH:16]([CH3:15])[CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -40 °C

Procedure

1-benzyloxymethylimidazole prepared according to the procedure of Ngochindo, R., J. Chem. Res. (S), 58 (1990)) (3.76 g, 20 mmol), and THF (40 mL) at -40° C., was treated dropwise with n-BuLi (8.4 mL, 21 mmol, 2.5M in hexane). The resulting solution was stirred at -40° C. for 15 min, and i-butyraldehyde (2.0 mL, 22 mmol) was added dropwise. The reaction was stirred at -40° C. for 1.5 h, 0° C. for 1 h, warmed to 23° C., poured into H2O, and extracted with EtOAc. The combined ekhracts were washed with brine, dried (Na2 SO4) and concentrated in vacuo. Trituration of the residue with Et2O/hexane gave a white solid which was dried in vacuo overnight to afford of the title compound (3.57 g, 69%). 1H NMR(CDCl3, 400 MHz) δ 7.28 (m, 5H), 6.97 (s, 1H), 6.92 (s, 1H), 5.23 (d, 1H, J=12 Hz), 5.42 (d, 1H, J=12 Hz), 4.48 (s, 2H), 4.44 (d, 1H, J=9 Hz), 2.21 (m, 1H), 1.02 (d, 3H, J=7 Hz), 0.83 (d, 3H, J=7 Hz).

Workup

stirringThe reaction was stirred at -40° C. for 1.5 h, 0° C. for 1 h
temperaturewarmed to 23° C.
extractionextracted with EtOAc
washThe combined ekhracts were washed with brine
customdried (Na2 SO4)
concentrationconcentrated in vacuo
customTrituration of the residue with Et2O/hexane gave a white solid which
customwas dried in vacuo overnight

Sources & evidence

ORD record: ord-9364a4a06ced401991545a8820488b8f
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05733882

Reaction notes

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