Nitrogen → 1-[5-(4-Nitro-pyrazol-1-ylmethyl)-furan-2-yl]-ethanol

HRID 2064917Notes

Reaction equation

N#N.[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[O:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=2)[CH:10]=1)([O-:5])=[O:4].[CH3:19][Mg]Br.[NH4+].[Cl-]>C1COCC1>[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[O:16][C:15]([CH:17]([OH:18])[CH3:19])=[CH:14][CH:13]=2)[CH:10]=1)([O-:5])=[O:4]

Participants

Conditions

Temperature: -78 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(4-nitro-pyrazol-1-ylmethyl)-furan-2-carbaldehyde (3.79 g, 17.14 mmol) in THF (173.0 mL) was treated at −78° C. with methylmagnesium bromide (17.1 mL of a 1M solution in THF, 17.14 mmol). The reaction mixture was stirred at −78° C. for 4 h then poured on sat. aq. NH4Cl (150 mL) and extracted with EA (2×300 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (50:50 hept-EA) gave the title compound as a yellow oil. TLC: rf (50:50 hept-EA)=0.24. LC-MS-conditions 02: tR=0.79 min. 1H NMR (400 MHz, CDCl3) δ 1.55 (d, J=6.5 Hz, 3H), 2.09 (d, J=5.0 Hz, 1H), 4.83-4.95 (m, 1H), 5.31 (s, 2H), 6.28 (d, J=3.0 Hz, 1H), 6.46 (d, J=3.0 Hz, 1H), 8.09 (s, 1H), 8.13 (s, 1H).

Workup

extractionextracted with EA (2×300 mL)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (50:50 hept-EA)

Sources & evidence

ORD record: ord-a2b0600b850f4c43b804bb824707e5b6
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288419B2

Reaction notes

Loading…