alpha-Angelica lactone → 3-acetonyl-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

HRID 26420

Reaction equation

HRID 26420 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH2:13][CH2:12][CH2:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.[CH3:14][C:15]1[O:20][C:18](=[O:19])[CH2:17][CH:16]=1>C1(C)C=CC=CC=1>[CH2:16]([C:17]1[C:18](=[O:19])[NH:10][CH2:11][CH2:12][CH2:13][C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[C:15]([CH3:14])=[O:20]

Participants

4

Reactant 2

HCID 11559alpha-Angelica lactone2×HCID 120090515-(3-methoxyphenyl)-3,4-dihydro-2H-pyrrole

Product 1

HCID 203329343-acetonyl-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The starting material is prepared as follows: The solution of 70 g of 2-(3-methoxyphenyl)-1-pyrroline [J. Org. Chem. 23, 1278, 1281 (1958)] and 43.2 g of α-angelicalactone in 600 ml of toluene is refluxed overnight. A second portion of 43.2 g of α-angelicalactone is added, the mixture is again refluxed overnight, cooled and evaporated. The residue is crystallized from 50 ml of ethyl acetate, to yield the 3-acetonyl-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone, melting at 140°-142°.

Workup

  1. customThe starting material is prepared
  2. temperaturecooled
  3. customevaporated
  4. customThe residue is crystallized from 50 ml of ethyl acetate

Sources & evidence

ORD record
ord-811a6d3800664a58b1f7f400a25bf363
Source dataset
uspto-grants-1979_04
Patent number
US04150129

Linked notes

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