Sodium hydride → HCID 22236208, compound

HRID 1744149Notes

Reaction equation

HRID 1744149 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH:12]([CH2:18][C:19]1([CH3:22])[CH2:21][CH2:20]1)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:12]([CH2:18][C:19]2([CH3:22])[CH2:20][CH2:21]2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 660494-BromothiophenolHCID 22235832HCID 22235832, compound

Product 1

HCID 22236208HCID 22236208, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cold solution of 4-bromothiophenol (455 mg, 2.4 mmol) in DRY (3 mL) was added sodium hydride (101 mg of 60% oil disp., 2.5 mmol). The resulting suspension was stirred at 0° C. for 30 min. A solution of ethyl 2-bromo-3-(1-methylcyclopropyl)propanoate (465 mg, 2.0 mmol) in DMF (2 mL) was added dropwise and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was partitioned between EtOAc and water. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography using Et2O in hexane to afford ethyl 2-[(4-bromophenyl)thio]-3-(1-methylcyclopropyl)propanoate.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-43750b755569494c8b1e81a9721968e2
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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