Tributylstannane → HCID 14757118, compound

HRID 2191010Notes

Reaction equation

HRID 2191010 reaction equation
N1(C(O[CH:9]2[CH:16]3[CH:12]([O:13][C:14]([CH3:18])([CH3:17])[O:15]3)[O:11][CH:10]2[CH2:19][O:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=S)C=CN=C1.CCCC[SnH](CCCC)CCCC.CC(N=NC(C#N)(C)C)(C#N)C>C1(C)C=CC=CC=1>[CH3:17][C:14]1([CH3:18])[O:13][CH:12]2[O:11][CH:10]([CH2:19][O:20][C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:9][CH:16]2[O:15]1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 57662106HCID 57662106, compound

Product 1

HCID 14757118HCID 14757118, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Compound 9.3 (5.5 g, 13.6 mmol) in toluene (20 mL) was added dropwise to a refluxing solution of Bu3SnH (6.7 mL, 24.0 mmol) and AIBN (300 mg, 1.8 mmol) in toluene (80 mL) under N2. The mixture was stirred for 2 h then cooled. The solution was partitioned between MeCN (300 mL) and hexanes (3×200 mL). The combined hexanes fractions were extracted with MeCN (200 mL), then the combined MeCN fractions were concentrated in vacuo and the residue was treated to silica gel column chromatography (SiO2, 4×20 cm, 35-75% EtOAc-hexanes gradient) to afford compound 9.4 (1.7 g, 46% yield). (Taken from: De Bernardo, S.; Tengi, J. P.; Sasso, G. J.; Weigele, J. Org. Chem. 1985, 50, 3457-3462.)

Workup

  1. temperaturethen cooled
  2. customThe solution was partitioned between MeCN (300 mL) and hexanes (3×200 mL)
  3. extractionThe combined hexanes fractions were extracted with MeCN (200 mL)
  4. concentrationthe combined MeCN fractions were concentrated in vacuo
  5. additionthe residue was treated to silica gel column chromatography (SiO2, 4×20 cm, 35-75% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-4b4a6c77b20f49f28c938f4b04633928
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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