Ethyl bromoacetate → HCID 18367297, compound

HRID 1741420Notes

Reaction equation

HRID 1741420 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). MS (m/z): 551 (M+ +1) NMR (CDCl3, δ): 1.18-1.40 (4H, m), 1.52-2.98 (18H, m), 3.90-4.70 (6H, m), 6.34-7.60 (11H, m)

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-321975c40a15489e896f6091a4492dc4
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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