Allyltributylstannane → HCID 67516171, compound

HRID 2173183Notes

Reaction equation

HRID 2173183 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH2:12][CH2:13][CH3:14].[CH2:15]([Sn](CCCC)(CCCC)CCCC)[CH:16]=[CH2:17].[Cl-].[Li+]>CCOC(C)=O>[CH2:17]([C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH2:12][CH2:13][CH3:14])[CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 67516032HCID 67516032, compound

Product 1

HCID 67516171HCID 67516171, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a flask charged with 5-bromo-4-propyl-2-benzofuran-1(3H)-one (130 mg, 0.51 mmol) and a stir bar was added allyl tri-n-butyltin (0.24 mL, 0.76 mmol), PdCl2(dppf)-DCM complex (42 mg, 0.051 mmol), lithium chloride (65 mg, 1.5 mmol), and tolene (5 mL). The mixture was sealed with a condensor, purged with nitrogen three times, and heated to reflux for 5 hours. The crude reaction was diluted with EtOAc, adsorbed onto silica gel, and purified by MPLC. Removal of solvent gave rise to 5-allyl-4-propyl-2-benzofuran-1(3H)-one (60 mg, 44% yield) as a light yellow oil.

Workup

  1. customThe mixture was sealed with a condensor
  2. custompurged with nitrogen three times
  3. temperatureheated
  4. temperatureto reflux for 5 hours
  5. customThe crude reaction
  6. custompurified by MPLC
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-37a173d85c064e6999425ae9ac477c2c
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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