Water → HCID 20244216, compound

HRID 482954Notes

Reaction equation

HRID 482954 reaction equation
C[CH:2]([C:6]1[CH:21]=[CH:20][C:9]2[O:10][CH2:11][C:12]3[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=3[C:14](=[O:15])[C:8]=2[CH:7]=1)[C:3]([OH:5])=[O:4].[C:22]([O-])([O-])=O.[K+].[K+].Br[CH2:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31].O>CN(C)C=O>[CH3:22][CH:11]1[O:10][C:9]2[CH:20]=[CH:21][C:6]([CH2:2][C:3]([O:5][CH2:29][C:30]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])=[O:4])=[CH:7][C:8]=2[C:14](=[O:15])[C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 418682-(11-Oxo-6,11-dihydrodibenzo[b,e]oxepin-2-yl)propanoic acidHCID 62576Benzyl bromoacetate

Product 1

HCID 20244216HCID 20244216, compoundYield 125.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 7.09 g (0.025 m) of 6,11-dihydro-α-methyl-11-oxodibenz[b,e]oxepin-2-acetic acid, and 2.59 g (0.0188 m) of anhydrous K2CO3 in 70 ml of dimethylformamide was warmed at 50° C. for one hour in an atmosphere of nitrogen. To this mixture 6.32 g (0.276 m) of benzyl bromoacetate was added dropwise and the mixture was held at 50° C. overnight (about 16 hours). The reaction mixture was poured into water and extracted with ether. The ether extract was washed with 5% NaHCO3, dried over Na2SO4, filtered and evaporated to give 10.11 g (94%) of an oil of (±)-2-phenylmethoxy-2-oxoethyl 6,11-dihydro-α-methyl-11-oxodibenz[b,e]oxepin-2-acetate.

Workup

  1. custom(about 16 hours)
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed with 5% NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9a1b24e0556b46b78be840b134967971
Source dataset
uspto-grants-1986_03
Patent number
US04576960

Reaction notes

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