Sodium Iodide → HCID 53788388, compound

HRID 1432883Notes

Reaction equation

HRID 1432883 reaction equation
C([O-])(O)=O.[Na+].[Na+].[I-].Br[C:9]1[S:13][C:12]([Cl:14])=[CH:11][CH:10]=1.[CH2:15]([OH:18])[CH:16]=[CH2:17]>CN(P(N(C)C)(N(C)C)=O)C.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:14][C:12]1[S:13][C:9]([CH2:17][CH2:16][CH:15]=[O:18])=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 7858Allyl AlcoholHCID 761332-Bromo-5-chlorothiopheneHCID 516892Sodium Bicarbonate

Product 1

HCID 53788388HCID 53788388, compoundYield 20.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of Pd(OAc)2 (0.12 g, 0.53 mmol), NaHCO3 (0.52 g, 6.19 mmol) and NaI (0.28 g, 1.87 mmol) in 5 mL of HMPA is added 5-bromo-2-chloro-thiophene (1.00 g, 5.06 mmol) and allyl alcohol (1.03 mL, 15.2 mmol). The mixture is heated to 90° C. and stirred for 16 hours. The reaction mixture is cooled to room temperature, diluted with Et2O and washed with water. The organic layer is dried over MgSO4, filtered and concentrated in vacuo. The crude residue is purified by flash column chromatography eluting with a gradient of 10% Et2O/hexanes to 20% Et2O/hexanes to provide the product (0.18 g, 1.03 mmol) as an oil. 1H NMR (CDCl3, 300 MHz) δ9.81 (s, 1H), 6.71 (d, 1H), 6.58 (d, 1H), 3.07 (t, 2H), 2.81 (t, 2H).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. washwashed with water
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue is purified by flash column chromatography
  7. washeluting with a gradient of 10% Et2O/hexanes to 20% Et2O/hexanes

Sources & evidence

ORD record
ord-3a62767deb3a4916a6a8a10d3e00875f
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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