Tributylstannane → Stannane, tributyl-1-cyclohexen-1-yl-

HRID 1176660Notes

Reaction equation

HRID 1176660 reaction equation
[CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1.[CH3:7][CH2:8][CH2:9][CH2:10][SnH:11]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH3:15]>C1C=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>[C:2]1([Sn:11]([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH2:9][CH2:8][CH3:7])[CH2:1][CH2:6][CH2:5][CH2:4][CH:3]=1

Participants

5

Reactant 2

HCID 5948TributylstannaneHCID 116051,3-Cyclohexadiene

Product 1

HCID 11783615Stannane, tributyl-1-cyclohexen-1-yl-Yield 235%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 1,3-cyclohexadiene (0.96 g, 12 mmol, d=0.84, 1143 uL) and Pd(PPh3)4 (462.2 mg, 0.4 mmol) in benzene (10 mL) under nitrogen atmosphere, was added Bu3SnH (1.16 g, 4 mmol, d=1.098, 1.06 mL) dropwise at room temperature and stirred for 15 minutes. After the solvent was removed on rotavap, the product was purified on silica flash chromatography (column 1.5 cm ID×20 cm) using a solvent gradient of 10:0 (100 mL) to 19:1(100 mL) to 9:1 (100 mL) of hexanes/EtOAc to afford cyclohexenyltributyltin (3.5 g, 9.4 mmol, 78.6% yield) as a clear liquid. Cyclohexenyltributyltin was characterized by 1H-NMR (CDCl3, 500 MHz). See FIG. 51.

Workup

  1. customAfter the solvent was removed on rotavap
  2. customthe product was purified on silica flash chromatography (column 1.5 cm ID×20 cm)

Sources & evidence

ORD record
ord-4713ef9262ac41f38f6aeed44399d263
Source dataset
uspto-grants-2010_11
Patent number
US07842814B2

Reaction notes

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