Acifran → HCID 12840342, compound

HRID 1389556Notes

Reaction equation

HRID 1389556 reaction equation
[CH3:1][C:2]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][C:3]1=[O:10].[CH3:17]OC(C1OC(C(C)C)(C2C=CC=CC=2)C(=O)C=1)=O.COC(C1OC(C2C=CC(Cl)=CC=2)(C)C(=O)C=1)=O.COC(C1OC(C)(C)C(=O)C=1)=O.COC(C1OC(CCCC)(CC)C(=O)C=1)=O.COC(C1OC(C2C=CC=CC=2)(C2C=CC=CC=2)C(=O)C=1)=O.COC(C1OC(C2CCCCC2)(CCC)C(=O)C=1)=O.COC(C1OC(COCC)(C2C=CC=C(OC)C=2)C(=O)C=1)=O.COC(C1OC(C2C=CC(CC)=C(CC)C=2)(C2C=CC([N+]([O-])=O)=CC=2)C(=O)C=1)=O.COC(C1OC(C2CCCC2)(CCCOCC)C(=O)C=1)=O>>[CH3:17][O:8][C:7]([C:5]1[O:6][C:2]([CH3:1])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3](=[O:10])[CH:4]=1)=[O:9]

Participants

11

Reactant 10

HCID 51576AcifranHCID 53695856HCID 53695856, compoundHCID 53725505HCID 53725505, compoundHCID 53824439HCID 53824439, compoundHCID 53830695HCID 53830695, compoundHCID 53895398HCID 53895398, compoundHCID 53897636HCID 53897636, compoundHCID 53999736HCID 53999736, compoundHCID 54058803HCID 54058803, compoundHCID 54530193HCID 54530193, compound

Product 1

HCID 12840342HCID 12840342, compound

Procedure

Similarly, but replacing 4,5-dihydro-5-methyl-4-oxo-5-phenylfuran-2-carboxylic acid with an equivalent amount of another compound of formula I described in Example 4, the following compounds of formula I are obtained, respectively: 4,5-dihydro-5-(1-methylethyl)-4-oxo-5-phenylfuran-2-carboxylic acid methyl ester; 5-(4-chlorophenyl)-4,5-dihydro-5-methyl-4-oxofuran-2-carboxylic acid methyl ester; 4,5-dihydro-5,5-dimethyl-4-oxofuran-2-carboxylic acid methyl ester, mp 66° C., ir(CHCl3)1720, 1695 and 1575 cm-1 ; spiro[furan-5(4H),1'(2'H)-naphthalene]-3',4'-dihydro-4-oxo-2-carboxylic acid methyl ester; 5-butyl-5-ethyl-4,5-dihydro-4-oxofuran-2-carboxylic acid methyl ester; 4,5-dihydro-4-oxo-5,5-diphenylfuran-2-carboxylic acid methyl ester; 5-cyclohexyl-4,5-dihydro-4-oxo-5-propylfuran-2-carboxylic acid methyl ester; 4,5-dihydro-5-ethoxymethyl-5-(3-methoxyphenyl)-4-oxofuran-2-carboxylic acid methyl ester; 4,5-dihydro-5-(3,4-diethylphenyl)-5-(4-nitrophenyl)-4-oxofuran-2-carboxylic acid methyl ester; 1,7-dioxaspiro[4,4]non-2-ene-4-oxo-2-carboxylic acid methyl ester; 1-oxaspiro[4,5]dec-2-ene-4-oxo-2-carboxylic acid methyl ester; spiro[furan-5-(4H),1'-indan]-4-oxo-2-carboxylic acid methyl ester; and 5-cyclopentyl-4,5-dihydro-5-(3-ethoxypropyl)-4-oxofuran-2-carboxylic acid methyl ester.

Workup

  1. customthe following compounds of formula I are obtained

Sources & evidence

ORD record
ord-54391249e848401abf50bbe35d69addd
Source dataset
uspto-grants-1981_01
Patent number
US04244958

Reaction notes

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