Allyltributylstannane → HCID 10976292, compound

HRID 1844075Notes

Reaction equation

HRID 1844075 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].[CH2:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[CH2:15]>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>[CH2:15]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:14]=[CH2:13]

Participants

5

Reactant 2

HCID 90628AllyltributylstannaneHCID 640185Methyl 2-(2-iodophenyl)acetate

Product 1

HCID 10976292HCID 10976292, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of methyl 2-iodophenylacetate (1.00 g, 3.62 mmol, prepared from the corresponding acid according to litt. Tetrahedron 63, 2007, 9979) in toluene (45 mL) was added Tetrakis(triphenylphosphine)palladium (209 mg, 0.0.181 mmol) and allyl tributylstannane (1.35 mL, 4.34 mmol). The resulting solution was heated to 110° C. for 20 h and then cooled down. The solvents were removed in vacuo. The yellow oil was partitioned between acetonitrile (30 mL) and hexane (30 mL) and the acetonitrile layer was washed with hexane (2*30 mL). The acetonitrile was removed in vacuo and the residue was purified by flash chromatography eluting with cyclohexane and ethyl acetate (15/1) to give Methyl 2-allylphenylacetate (colourless oil, 446 mg, 65%). C12H14O2; MW: 190.24; LCMS (method A) RT 1.74 min; ES: 191 (100%, MH+); IR. 2951, 1734 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.14-7.41 (4H, m), 5.99 (1H, m), 5.12 (1H, m), 5.03 (1H, m), 3.73 (3H, s), 3.72 (2H, s), 3.47 (2H, dt) ppm.

Workup

  1. temperaturecooled down
  2. customThe solvents were removed in vacuo
  3. customThe yellow oil was partitioned between acetonitrile (30 mL) and hexane (30 mL)
  4. washthe acetonitrile layer was washed with hexane (2*30 mL)
  5. customThe acetonitrile was removed in vacuo
  6. customthe residue was purified by flash chromatography
  7. washeluting with cyclohexane and ethyl acetate (15/1)

Sources & evidence

ORD record
ord-f58ad7c66031475eacbc5f4d5fd0b176
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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