Ethyl bromoacetate → HCID 18367297, compound

HRID 380155Notes

Reaction equation

HRID 380155 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:20]3[CH2:24][CH2:23][CH2:22][N:21]3[CH:25]3[C:34]4[C:29](=[C:30]([OH:35])[CH:31]=[CH:32][CH:33]=4)[CH2:28][CH2:27][CH2:26]3)[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.Br[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:20]3[CH2:24][CH2:23][CH2:22][N:21]3[CH:25]3[C:34]4[C:29](=[C:30]([O:35][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:31]=[CH:32][CH:33]=4)[CH2:28][CH2:27][CH2:26]3)[O:11][C:12]=2[C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 18367254HCID 18367254, compound

Product 1

HCID 18367297HCID 18367297, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[2-[4,5-bis(4-methylphenyl)oxazol-2-yl]pyrrolidin-1-yl]-1,2,3,4-tetrahydro-5-hydroxynaphthalene (0.13 g) and ethyl bromoacetate (0.10 g) in DMF (5 ml) was added K2CO3 (0.13 g). After being stirred for 2 days at room temperature, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine. The dried solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give 1-[2-[4,5-bis(4-methylphenyl)oxazol-2-yl]pyrrolidin-1-yl]-1,2,3,4-tetrahydro-5-ethoxycarbonylmethoxynaphthalene (0.13 g).

Workup

  1. customthe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. customThe dried solvent was evaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1cc0b636c6644c8b82c8221766b8d9e2
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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