Sodium ethoxide → (cis)-4-(3,4-Dimethoxyphenyl)-2-(2-(2-methoxyphenyl)-2-oxoethyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-one

HRID 1871384Notes

Reaction equation

HRID 1871384 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C@H:20]3[C@H:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)[C:14](=[O:21])[NH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:22]([O-:24])C.[Na+].Br[CH:27](OC)[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C@H:20]3[C@H:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)[C:14](=[O:21])[N:13]([CH2:27][C:28]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=3[O:24][CH3:22])=[O:29])[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxide2×HCID 10913208(cis)-4-(3,4-Dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-oneHCID 15556716Methoxyphenacylbromide2×

Product 1

HCID 70303751(cis)-4-(3,4-Dimethoxyphenyl)-2-(2-(2-methoxyphenyl)-2-oxoethyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 2 g of compound 1 and 1 eq sodium ethanolate in 30 ml of dimethylformamide was added to a solution of 2 g of ω-bromo-2-methoxyacetophenone in dimethylformamide. After 30 min small portions of additional ω-bromo-2-methoxyacetophenone (total 5 gram) and sodium ethanolate were added during 2 hours. Subsequently the reaction mixture was evaporated and the residue partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate and evaporated. The residue was purified by chromatography (dichloromethane). Crystallized from methanol. M.p. 93°-96° C.

Workup

  1. customSubsequently the reaction mixture was evaporated
  2. customthe residue partitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by chromatography (dichloromethane)
  6. customCrystallized from methanol

Sources & evidence

ORD record
ord-fd90fce93e6642029d77b77bc6ac9653
Source dataset
uspto-grants-2000_08
Patent number
US06103718

Reaction notes

Loading…