Benzene → Methyl 4-amino-5-butyryl-1-hydroxycyclohexa-2,4-diene-1-carboxylate

HRID 349036Notes

Reaction equation

HRID 349036 reaction equation
[NH2:1][C:2]1[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1.C=C[C:13](=[O:17])[CH2:14][CH2:15][CH3:16].[CH:18]1C=CC=C[CH:19]=1>>[NH2:1][C:2]1[CH:18]=[CH:19][C:5]([OH:6])([C:7]([O:9][CH3:10])=[O:8])[CH2:4][C:3]=1[C:13](=[O:17])[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 241BenzeneHCID 153951-Hexen-3-oneHCID 5072225Methyl 5-aminofuran-2-carboxylate

Product 1

HCID 21086195Methyl 4-amino-5-butyryl-1-hydroxycyclohexa-2,4-diene-1-carboxylate

Procedure

A stirred solution of methyl 5-amino-2-furoate (1.4 g, 10 mmol) and 1-hexen-3-one (7 mL, 60 mmol) in benzene (50 mL) was heated to reflux for 2 h. The reaction mixture was concentrated under reduced pressure to afford a crude oil. Purification by flash column chromatography (silica, 2:1 hexanes/ethyl acetate) provided methyl 4-amino-5-butyryl-1-hydroxycyclohexa-2,4-diene-1-carboxylate (1.25 g): 1H NMR (300 MHz, CDCl3): δ 6.26–6.23 (m, 1H), 6.09–6.05 (m, 1H), 3.80 (s, 3H), 3.02–2.96 (m, 1H), 2.89–2.84 (m, 1H), 2.42–2.37 (m, 2H) 1.64–1.57 (m, 2H), 0.96–0.88 (m, 3H).

Workup

  1. temperatureto reflux for 2 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto afford a crude oil
  4. customPurification by flash column chromatography (silica, 2:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-8150968c79d2423c81034c50f5e7b8fd
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

Loading…