1,3-Diphenyl-2-propanone → 3,5-diphenyl-4H-pyran-4-one

HRID 867036

Reaction equation

[Na][Na].O[CH:4]=[C:5]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:6](=[O:16])[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH:8][OH:9].C1(CC(=O)CC2C=CC=CC=2)C=CC=CC=1.C(OCC)=O.C[O-].[Na+].CC(=O)C=C=C>>[C:10]1([C:7]2[C:6](=[O:16])[C:5]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:4][O:9][CH:8]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 6

HCID 75931,3-Diphenyl-2-propanone

HCID 8025Ethyl formate

HCID 141233Disodium

HCID 109313673,4-Pentadien-2-one

HCID 10942334Sodium Methoxide

HCID 705837841,5-Dihydroxy-2,4-diphenyl-1,4-pentadien-3-one

Product 1

HCID 2821893,5-diphenyl-4H-pyran-4-one

Procedure

Benary and Bitter, Ber. 61, 1058 (1928) taught the synthesis of an intermediate disodium salt of 1,5-dihydroxy-2,4-diphenyl-1,4-pentadien-3-one by the condensation of 1,3-diphenyl-2-propanone with ethyl formate in the presence of sodium methoxide. The intermediate pentadienone is neutralized with strong acid to form 3,5-diphenyl-4-pyrone. Reaction of the pyrone with ammonium acetate at an elevated temperature produces 3,5-diphenyl-4(1H)-pyridinone.

Sources & evidence

ORD record: ord-19cfcc77db2d4972b85e37433e3d1a52
Source dataset: uspto-grants-1978_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04102669

Linked notes

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