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Water → HCID 67257850, compound

HRID 2371054
Notes
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Reaction equation

HRID 2371054 reaction equation
[Br:1][C:2]1[S:3][C:4]([Br:13])=[CH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Li+].[CH3:15][CH:16]([N-]C(C)C)C.O1CC1.O>C1COCC1>[Br:13][C:4]1[S:3][C:2]([Br:1])=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:5]=1[CH2:15][CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6354Ethylene OxideHCID 2724682Lithium diisopropylamideHCID 45712422,5-Dibromo-3-phenylthiophene

Product 1

HCID 67257850HCID 67257850, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-65 °C

Procedure

To a solution of 2,5-dibromo-3-phenylthiophene (2.54 g, 8.0 mmol) in dry THF (30 mL) at −65° C. was added LDA (8.8 mmol) dropwise. After stirring for 30 min at −65° C., oxirane (20.0 mmol) was added and the reaction was stirred for 2 h. The reaction mixture was then warmed to room temperature and water was added. The resulting mixture was extracted with EtOAc (3×100 mL), washed with brine, and dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound.

Workup

  1. stirringthe reaction was stirred for 2 h
  2. temperatureThe reaction mixture was then warmed to room temperature
  3. extractionThe resulting mixture was extracted with EtOAc (3×100 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-39eb8b49baed460d91e9b42f5f840ba0
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08710245B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes