Diethyl 2-methyl-2-(3-nitrophenoxy)malonate → 4-(4-Aminophenoxymethyl)-2-methoxycarbonyl-furan

HRID 226620Notes

Reaction equation

HRID 226620 reaction equation
CC(OC1C=CC=C([N+]([O-])=O)C=1)(C(OCC)=O)C(OCC)=O.[N+:23]([C:26]1[CH:42]=[CH:41][C:29]([O:30][CH2:31][C:32]2[CH:33]=[C:34]([C:37]([O:39][CH3:40])=[O:38])[O:35][CH:36]=2)=[CH:28][CH:27]=1)([O-])=O>>[NH2:23][C:26]1[CH:27]=[CH:28][C:29]([O:30][CH2:31][C:32]2[CH:33]=[C:34]([C:37]([O:39][CH3:40])=[O:38])[O:35][CH:36]=2)=[CH:41][CH:42]=1

Participants

3

Reactant 2

HCID 22060402Diethyl 2-methyl-2-(3-nitrophenoxy)malonateHCID 220610744-(4-Nitrophenoxymethyl)-2-methoxycarbonyl-furan

Product 1

HCID 220608754-(4-Aminophenoxymethyl)-2-methoxycarbonyl-furan

Procedure

In like manner to the reduction of diethyl 2-methyl-2-(3-nitrophenoxy)malonate, 4-(4-nitrophenoxymethyl)-2-methoxycarbonyl-furan was reduced to provide 4-(4-aminophenoxymethyl)-2-methoxycarbonyl-furan. 1H NMR (CDCl3): δ 7.15 (d, 1H, J=3.5 Hz), 7.05 (t, 1H, J=8.2 Hz), 6.50 (d, 1H, J=3.5 Hz), 6.37–6.27 (m, 3H), 5.01 (s, 2H), 3.89 (s, 3H).

Sources & evidence

ORD record
ord-9e830ae982754eb887be8ca964efa305
Source dataset
uspto-grants-2009_07
Patent number
US07557210B2

Reaction notes

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