Potassium Carbonate → Methyl (4-(2-(diphenylmethoxy)ethyl)-3,4-dihydro-2H-1,4-benzoxazin-8-yloxy)acetate

HRID 2186746Notes

Reaction equation

HRID 2186746 reaction equation
[C:1]1([CH:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:8][CH2:9][CH2:10][N:11]2[C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([OH:21])[C:15]=3[O:14][CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][C:36]([O:38][CH3:39])=[O:37].[Cl-].[NH4+]>CN(C=O)C>[C:22]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH2:9][CH2:10][N:11]2[C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH2:35][C:36]([O:38][CH3:39])=[O:37])[C:15]=3[O:14][CH2:13][CH2:12]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 213498804-(2-(diphenylmethoxy)ethyl)-8-hydroxy-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 21349893Methyl (4-(2-(diphenylmethoxy)ethyl)-3,4-dihydro-2H-1,4-benzoxazin-8-yloxy)acetateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2-(diphenylmethoxy)-ethyl)-8-hydroxy-3,4-dihydro-2H-1,4-benzoxazine (161 mg) was dissolved in anhydrous DMF (4 ml), and anhydrous potassium carbonate (54 mg) and methyl bromoacetate (0.04 ml) were added to the resultant solution, and the mixture was stirred at room temperature overnight. The reaction solution was poured into a saturated ammonium chloride aqueous solution, and then extracted with ethyl acetate containing 15% n-hexane. The resultant organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated. The resultant residue was purified by medium-pressure column chromatography (solvent:ethyl acetate:cyclohexane=1/3) to obtain the colorless oily object compound (118 mg, yield 97%).

Workup

  1. extractionextracted with ethyl acetate containing 15% n-hexane
  2. washThe resultant organic layer was washed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resultant residue was purified by medium-pressure column chromatography (solvent:ethyl acetate:cyclohexane=1/3)

Sources & evidence

ORD record
ord-8be4682920664676a90922828387c781
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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