Allyltributylstannane → HCID 69087515, compound

HRID 2173207Notes

Reaction equation

HRID 2173207 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]2[C:6](=[O:10])[O:7][CH:8]([CH3:9])[C:4]=2[CH:3]=1.[Cl-].[Li+].[CH2:15]([Sn](CCCC)(CCCC)CCCC)[CH:16]=[CH2:17]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][CH:8]1[C:4]2[CH:3]=[C:2]([CH2:17][CH:16]=[CH2:15])[CH:12]=[CH:11][C:5]=2[C:6](=[O:10])[O:7]1

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 67516025HCID 67516025, compound

Product 1

HCID 69087515HCID 69087515, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

5-Bromo-3-methyl-2-benzofuran-1(3H)-one (1.00 g, 4.40 mmol) was dissolved in toluene (30 mL) treated with lithium chloride (0.560 g, 13.2 mmol), Pd(Ph3P)4 (0.254 g, 0.220 mmol), and allyl tributylstannane (1.75 g, 5.29 mmol). The reaction mixture was degassed and stirred at reflux under N2 for 3 h. The reaction mixture was poured into water and extracted with ethyl acetate; the organic layer was washed wtih brine 1×, dried and purified by MPLC eluting with 0-10% ethyl acetate/hexanes. to afford the title compound. 1H NMR (500 MHz, D-DMSO, δ in ppm): 7.75 (d, J=8 Hz, 1H), 7.50 (s, 1H), 7.42 (d, J=8 Hz, 1H), 6.00 (m, 1H), 5.66 (q, J=6.5 Hz, 1H), 5.13 (m, 2H), 3.53 (d, J=6.5 Hz, 2H), 1.54 (d, J=7 Hz, 3H).

Workup

  1. customThe reaction mixture was degassed
  2. temperatureat reflux under N2 for 3 h
  3. additionThe reaction mixture was poured into water
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was washed wtih brine 1×
  6. customdried
  7. custompurified by MPLC
  8. washeluting with 0-10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b5e73ce1c7a040bf8ba04bbed35a08a1
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…