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Sodium Iodide → 4-Methyl-1-thiophen-3-yl-pentan-3-one

HRID 1859522
Notes
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Reaction equation

HRID 1859522 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[CH3:7][CH:8]([CH3:13])[CH:9]([OH:12])[CH:10]=[CH2:11].[I-].[Na+].C(=O)(O)[O-].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH3:7][CH:8]([CH3:13])[C:9](=[O:12])[CH2:10][CH2:11][C:2]1[CH:6]=[CH:5][S:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 11776TriphenylphosphineHCID 133833-BromothiopheneHCID 209294-Methyl-1-penten-3-olHCID 516892Sodium Bicarbonate

Product 1

HCID 124772794-Methyl-1-thiophen-3-yl-pentan-3-one

Reagents, catalysts & solvents 2

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes
HCID 167845
palladium(II) acetate
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to General Method 4b using 3-bromothiophene (20 mmol), 4-methyl-1-penten-3-ol (30 mmol), sodium iodide (0.7 mmol), sodium bicarbonate (24 mmol), triphenylphosphine (0.6 mmol), DMF (15 mL), and palladium acetate (0.2 mmol). The title compound was flash chromatographed using EtOAc:hexane (5:95 to 10:90).

Workup

  1. customThe title compound was prepared
  2. customchromatographed

Sources & evidence

ORD record
ord-344f539b93384784a326a21ef037d6ff
Source dataset
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06528510B1

Reaction notes

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