Ethylene Glycol → 1-(2-methyl-1,3-dioxolan-2-yl-methyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

HRID 46516Notes

Reaction equation

HRID 46516 reaction equation
[O:1]=[C:2]([CH3:22])[CH2:3][C:4]1[C:5](=[O:21])[NH:6][CH2:7][CH2:8][CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=3)[C:10]=12.[CH2:23](O)[CH2:24][OH:25].B(F)(F)F.CCOCC.[OH-].[Na+]>C1C=CC=CC=1.O>[CH3:22][C:2]1([CH2:3][C:4]2[C:5](=[O:21])[NH:6][CH2:7][CH2:8][CH:9]3[CH2:18][CH2:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=4)[C:10]=23)[O:25][CH2:24][CH2:23][O:1]1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 128324091-(2-oxo-propyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Product 1

HCID 205556101-(2-methyl-1,3-dioxolan-2-yl-methyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

The starting material is prepared as follows: The mixture of 20 g of 1-(2-oxopropyl)-3,4,5,5a,6,7-hexahydro-9-methoxy-2H-naphth[1,2-d]azepin-2-one, 37.5 ml of ethylene glycol and 0.95 g of boron trifluoride etherate in benzene is refluxed under a water trap for 6 hours. It is cooled and 10 g of sodium hydroxide in 140 ml of water are added rapidly and the mixture is extracted with chloroform. The extract is dried, evaporated and the residue is crystallized from diethyl ether, to yield the 1-(2-methyl-1,3-dioxolan-2-yl-methyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one melting at 192°-194°.

Workup

  1. customThe starting material is prepared
  2. temperatureis refluxed under a water trap for 6 hours
  3. temperatureIt is cooled
  4. extractionthe mixture is extracted with chloroform
  5. customThe extract is dried
  6. customevaporated
  7. customthe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-a0a0e22347714b3aa0c04887ae6f819c
Source dataset
uspto-grants-1979_11
Patent number
US04173633

Reaction notes

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