Allyltributylstannane → HCID 69087510, compound

HRID 2173206Notes

Reaction equation

HRID 2173206 reaction equation
Br[C:2]1[S:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH3:11].[CH2:12]([Sn](CCCC)(CCCC)CC=C)[CH2:13][CH2:14]C.[Cl-].[Li+]>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:11][C:3]1[C:4]2[CH2:8][O:7][C:6](=[O:9])[C:5]=2[S:10][C:2]=1[CH2:14][CH:13]=[CH2:12]

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 67516471HCID 67516471, compound

Product 1

HCID 69087510HCID 69087510, compound

Reagents, catalysts & solvents 2

HCID 15220664Palladium--triphenylphosphane (1/1)CatalystHCID 1140TolueneSolvent

Procedure

In a 100 mL round bottom flask was added 2-bromo-3-methylthieno[2,3-c]furan-6-(4H)-one (60 mg, 0.257 mmol, 1.0 eq), tributyl (prop-2-en-1-yl)stannane (102 mg, 0.309 mmol, 1.2 eq), palladium triphenylphosphane (1:4) (14.9 mg, 0.013 mmol, 0.05 eq) and lithium chloride (32.7 mg, 0.77 mmol, 3.0 eq). The mixture was dissolved in toluene (20 mL), degassed and filled with N2. The mixture was reflux for 3 hr, concentrated, extracted with EtOAc, washed with water. The organic phase was dried over MgSO4, filtered and concentrated. The desired product was obtained after purification by flash column chromatography. LC-MS (IE, m/z): 195.3 [M+1]+; 1H NMR (500 MHz, CDCl3, δ in ppm): 5.16 (2H, s), 2.19 (3H, s).

Workup

  1. customdegassed
  2. additionfilled with N2
  3. temperatureThe mixture was reflux for 3 hr
  4. concentrationconcentrated
  5. extractionextracted with EtOAc
  6. washwashed with water
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f19ed5901d3b46a48a81d4ea47c50103
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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