Ethyl bromoacetate → HCID 18367225, compound

HRID 1741397Notes

Reaction equation

HRID 1741397 reaction equation
[Si:1]([O:18][C:19]1[CH:20]=[C:21]([CH2:25][CH2:26][C:27]([C:29]2[O:30][C:31]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:33]=2)=[O:28])[CH:22]=[CH:23][CH:24]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49].C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C.O>CN(C)C=O>[Si:1]([O:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=1)[CH2:25][CH:26]([C:27]([C:29]1[O:30][C:31]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[C:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:33]=1)=[O:28])[CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 18367286HCID 18367286, compoundHCID 22728543Water ethylacetate

Product 1

HCID 18367225HCID 18367225, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[3-(tert-butyldiphenylsilyloxy)phenyl]-1-(4,5-diphenyl-2-oxazolyl)-1-propanone (526 mg), ethyl bromoacetate (1.61 g), and K2CO3 (1.34 g) in N,N-dimethylformamide (2.0 ml) was stirred at room temperature for 5 hours and poured into ethyl acetate-water. The organic layer was separated, washed with water (three times) and brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed over silica gel to afford ethyl 3-[3-(tert-butyldiphenylsilyloxy)benzyl]-4-(4,5-diphenyl-2-oxazolyl)-4-oxobutyrate (436 mg) as an oil-(+) APCI-MS (m/z): 694 (M+ +1) IR (Nujol): 1740, 1700, 1600, 1580 cm-1

Workup

  1. customThe organic layer was separated
  2. washwashed with water (three times) and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-e8a4215e438d48d58c327769494fa713
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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