Tributylvinyltin → HCID 67171363, compound

HRID 1506359Notes

Reaction equation

HRID 1506359 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[C:11]1[O:10][N:9]=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH3:23])=[CH:17][CH:16]=3)[C:7]=1[CH2:6][CH2:5]2.[Cl-].[Li+].[CH2:26]([Sn](CCCC)(CCCC)C=C)[CH2:27]CC>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:21]([C:18]1[CH:17]=[CH:16][C:15]([C:8]2[C:7]3[CH2:6][CH2:5][C:4]4[C:12]([C:11]=3[O:10][N:9]=2)=[CH:13][CH:14]=[C:2]([CH:26]=[CH2:27])[CH:3]=4)=[CH:20][CH:19]=1)[CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 67171032HCID 67171032, compound

Product 1

HCID 67171363HCID 67171363, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To 7-bromo-3-(4-propylphenyl)-4,5-dihydronaphtho[2,1-d]isoxazole (Preparation 20C, 0.32 g, 0.869 mmol) in dioxane (3 mL) were added sequentially lithium chloride (0.111 g, 2.61 mmol) and tributyl(vinyl)stannane (0.251 mL, 0.869 mmol). The reaction mixture was purged with nitrogen gas for 3 min. Tetrakis(triphenylphosphine) palladium(0) (0.100 g, 0.087 mmol) was added and the resulting yellow solution was purged with nitrogen gas for 2 min., and heated at 100° C. for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography using hexane/ethyl acetate. Fractions corresponding to the desired product were collected and concentrated to yield 3-(4-propylphenyl)-7-vinyl-4,5-dihydronaphtho[2,1-d]isoxazole (0.205 g, 0.650 mmol, 74.8% yield) as a pale yellow solid. LCMS M+1=316.2.

Workup

  1. customThe reaction mixture was purged with nitrogen gas for 3 min
  2. customthe resulting yellow solution was purged with nitrogen gas for 2 min.
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customFractions corresponding to the desired product were collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1807652bf88d42138daa133c7050c343
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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