Diethyl Ether → HCID 86586483, compound

HRID 843049Notes

Reaction equation

HRID 843049 reaction equation
O=[C:2]([CH3:23])[CH:3]([C:14]1[C:15](=O)[C:16](=[O:21])[C:17]=1[O:18]CC)[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1.[NH2:24][CH:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH3:26].C([O:33]CC)C>C(O)C>[O:33]=[CH:23][CH2:2][CH:3]([C:14]1[C:17](=[O:18])[C:16](=[O:21])[C:15]=1[NH:24][CH:25]([CH3:26])[C:27]([CH3:30])([CH3:29])[CH3:28])[C:4]1[CH:5]=[CH:6][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 5209072-Butanamine, 3,3-dimethyl-HCID 12051835HCID 12051835, compound

Product 1

HCID 86586483HCID 86586483, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[2-Oxo-1-(4-trifluoromethyl-phenyl)-propyl]-4-ethoxy-cyclobut-3-ene-1,2-dione (0.350 g, 1.07 mmol) and 2-amino-3,3-dimethylbutane (0.13 mL, 0.998 mmol) were stirred together in ethanol (6 mL) at room temperature overnight. Diethyl ether (25 mL) was added and the precipitated product was collected by filtration. It was stirred in diethyl ether/petroleum ether overnight, filtered and dried in vacuo to afford 0.15 g (37%) of desired product (1H NMR in CDCl3 suggested the presence of both the keto and enol forms in about an 8:1 ratio) as an off-white solid: m.p. 178.2-179.8° C.; 1H NMR (CDCl3) δ 11.74(s,1H), 7.73(ABq,2H), 7.39(ABq,2H), 3.92(m,1H), 1.86(s,3H), 0.93(d,3H), 0.69(s,9H); IR (KBr) 3310, 2970, 2600, 1775, 1710, 1560, 1395, 1260, 1160, 1125, 850 cm−1; MS (m/z) 381 [M+].

Workup

  1. filtrationthe precipitated product was collected by filtration
  2. filtrationfiltered
  3. customdried in vacuo

Sources & evidence

ORD record
ord-186c5b44785745b1a2343223100172ff
Source dataset
uspto-grants-2002_04
Patent number
US06376555B1

Reaction notes

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