Tetrahydrofuran → HCID 54496316, compound

HRID 1781630Notes

Reaction equation

HRID 1781630 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:11])[CH2:9][SH:10])([CH3:6])([CH3:5])[CH3:4].[CH3:12][O:13][C:14](=[O:25])[CH:15](Br)[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O1CCC[CH2:27]1>C(OCC)(=O)C>[CH2:12]([O:13][C:14](=[O:25])[CH:15]([S:10][CH2:9][C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:11])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:27]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 113555652-Methyl-2-propanyl sulfanylacetateHCID 15680624Methyl α-bromobenzenebutanoate

Product 1

HCID 54496316HCID 54496316, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2.3 g (53.2 mmol) of sodium hydride in the form of a suspension in mineral oil are placed at 0° in 30 ml of tetrahydrofuran. Then at 0° to 10°, 6.6 g (44.:3 mmol) of thioglycolic acid tert-butyl ester are added dropwise thereto. A viscous suspension is formed which is diluted with 50 ml of tetrahydrofuran. The mixture is then stirred for 20 minutes at 0° and then 12 g (44.3 mmol) of 2-bromo-4-phenyl-butyric acid methyl ester are added dropwise thereto. The mixture is stirred for 2 hours at room temperature, then taken up in 100 ml of ethyl acetate and extracted by shaking in succession with 50 ml of water and 50 ml of saturated sodium chloride solution. The aqueous phases are combined and extracted by shaking with 25 ml of ethyl acetate. The organic phases are combined, dried over sodium sulfate, filtered and concentrated by evaporation. Chromatography on silica g al with hexane/ethyl acetate (20:1) as eluant yields 5.7 g (38% of theory) of 2-tert-butyloxycabonylmethylthio-4-phenyl-butyric acid ethyl ester in the form of an oil.

Workup

  1. customA viscous suspension is formed which
  2. stirringThe mixture is stirred for 2 hours at room temperature
  3. extractionextracted
  4. stirringby shaking in succession with 50 ml of water and 50 ml of saturated sodium chloride solution
  5. extractionextracted
  6. stirringby shaking with 25 ml of ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-f96535ebed4f49b298075deda61158bb
Source dataset
uspto-grants-1997_05
Patent number
US05633379

Reaction notes

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