Tributylvinyltin → HCID 59514334, compound

HRID 1159179Notes

Reaction equation

HRID 1159179 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2Br)[CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH:17]([Sn](CCCC)(CCCC)CCCC)=[CH2:18].[F-].[K+]>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>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH:17]=[CH2:18])[CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 522689Potassium FluorideHCID 59514332HCID 59514332, compound

Product 1

HCID 59514334HCID 59514334, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A stream of argon was passed through a solution of 8-bromo-naphthalene-1-carboxylic acid ethyl ester (1.44 g) in toluene (15 ml) for 15 min. Then tetrakis(triphenylphosphine)palladium (179 mg) and vinyltributylstannane (1.65 ml) were added. The reaction mixture was heated under an Argon atmosphere to 100° C. overnight, then cooled to r.t. and treated with 4M potassium fluoride solution. The suspension was stirred for 10 min and then filtered. The solids were washed with toluene. The filtrate was washed with 4M KF solution, then dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient:cyclohexane→cyclohexane/EtOAc 3:2) to give 8-vinyl-naphthalene-1-carboxylic acid ethyl ester (1.11 g) as light yellow liquid. MS (ISP): 227.1 ((M+H)+).

Workup

  1. temperaturecooled to r.t.
  2. filtrationfiltered
  3. washThe solids were washed with toluene
  4. washThe filtrate was washed with 4M KF solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (silica gel; gradient:cyclohexane→cyclohexane/EtOAc 3:2)

Sources & evidence

ORD record
ord-ded318e3719c4c73b2213e47de4e42bd
Source dataset
uspto-grants-2010_10
Patent number
US07812047B2

Reaction notes

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