Sodium hydride → ethyl 3-amino-5-tert-butylfuran-2-carboxylate

HRID 1698908Notes

Reaction equation

HRID 1698908 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:17])([CH3:16])/[C:5](/[O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6]/[C:7]#[N:8].[NH4+].[Cl-]>C1COCC1>[NH2:8][C:7]1[CH:6]=[C:5]([C:4]([CH3:16])([CH3:17])[CH3:3])[O:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11218082HCID 11218082, compound

Product 1

HCID 11241292ethyl 3-amino-5-tert-butylfuran-2-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of sodium hydride (62 mg, 2.6 mmol, 1.1 equiv) in anh. THF (50 mL) was added (Z)-4,4-dimethyl-3-(ethoxycarbonylmethoxy)pentenenitrile (0.50 g, 2.4 mmol). The reaction mixture was stirred for 3 h, treated with a saturated aq. NH4Cl solution (2 mL), and concentrated under reduced pressure. The residue was purified by flash chromatography (50 g SiO2, 10% EtOAc/hex) to afford ethyl 3-amino-5-tert-butylfuran-2-carboxylate (0.44 g, 88%) as a white solid: mp 44-45° C.; TLC (10% EtOAc/hex) Rf0.19; 1H NMR (CDCl3) δ1.26 (s, 9H), 1.36 (t, J=7.0 Hz, 3H), 4.32 (q, J=7.0 Hz, 2H), 4.51 (br s, 2H), 5.75 (s, 1H); FAB-LRMS m/z (rel abundance) 212 (M+H, 100%). Anal. Calcd for C11H17NO3: C, 62.54; H, 8.11; N, 6.63. Found: C, 62.48; H, 8.06; N, 6.61.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by flash chromatography (50 g SiO2, 10% EtOAc/hex)

Sources & evidence

ORD record
ord-f8ef7be86d3d424abac2da2102224e3b
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

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