1-Bromo-2-methylpropane → HCID 68603776, compound

HRID 2189162Notes

Reaction equation

HRID 2189162 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:14])[CH3:13].BrCCOC.BrCC(C)C.C1N=CN(C(N2C=NC=C2)=O)C=1.[C:37]([NH:40][C:41]1[CH:49]=[CH:48][C:44]([C:45](O)=[O:46])=[CH:43][C:42]=1[CH2:50][CH3:51])(=[O:39])[CH3:38]>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:14])[CH3:13].[C:37]([NH:40][C:41]1[CH:49]=[CH:48][C:44]([C:45](=[O:46])[CH2:13][C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH2:3][O:2][CH3:1])=[O:14])=[CH:43][C:42]=1[CH2:50][CH3:51])(=[O:39])[CH3:38]

Participants

8

Reactant 5

HCID 65551-Bromo-2-methylpropaneHCID 682631,1'-CarbonyldiimidazoleHCID 809722-Bromoethyl methyl ether2×HCID 24711334HCID 24711334, compoundHCID 68605061HCID 68605061, compound

Product 2

HCID 24711334HCID 24711334, compoundHCID 68603776HCID 68603776, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A separated flask was charged with 1-(2-(2-methoxyethoxy)phenyl)ethanone (11.2 g, 57 mmol). (1-(2-(2-Methoxyethoxy)phenyl)ethanone was prepared by a procedure analogous to Example 1, in which commercially 1-bromo-2-methoxyethane was substituted for 1-bromo-2-methyl propane). The 1-bromo-2-methoxyethane was added to anhydrous THF (50 mL) and cooled to −78° C. To this solution was added commercially available lithium hexamethyl-silylamide (1M in hexanes, 172 mL, 172 mmol, Aldrich) over a 3 hour period at −78° C. The mixture was stirred for an additional 2 hours at −78° C. To the resulting mixture were added dropwise a solution of CDI and 4-acetamido-3-ethylbenzoic acid (above) at −78° C. The resulting mixture was stirred at −78° C. for an additional 30 min and subsequently allowed to warm up to room temperature over 12 h. The reaction was quenched with 1 N HCl and extracted with EtOAc and water. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography to give 1-(4-acetamido-3-ethylphenyl)-3-(2-(2-methoxyethoxy)phenyl)propane-1,3-dione as a white solid (11 g, 60%).

Workup

  1. stirringThe resulting mixture was stirred at −78° C. for an additional 30 min
  2. temperatureto warm up to room temperature over 12 h
  3. customThe reaction was quenched with 1 N HCl
  4. extractionextracted with EtOAc and water
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-4f7778f59e554506a614b27ec1e174b5
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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