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

HRID 14246Notes

Reaction equation

HRID 14246 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-b3c4f6e1572d4430b0ced6aa9ae5f0b0
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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