Dibutyltin oxide → HCID 178471344, compound

HRID 1927445Notes

Reaction equation

HRID 1927445 reaction equation
[C:1]([C:5]1[CH:39]=[CH:38][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=2)[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N:44]=[N+:45]=[N-:46])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:39]=[CH:38][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[NH:46][N:45]=[N:44][N:37]=3)=[CH:32][CH:31]=2)[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 57831393Ethyl E-8-[2-(4-tert-butylbenzyloxy)phenyl]-6-(4-cyanobenzyl)oct-7-enoate

Product 1

HCID 178471344HCID 178471344, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1000 mg (1.91 mmol) of ethyl (7E)-8-{2-[(4-tert-butylbenzyl)oxy]phenyl}-6-(4-cyanobenzyl)oct-7-enoate in 70 ml of toluene is mixed with 3.8 ml (28.6 mmol) of trimethylsilyl azide and 713 mg (2.86 mmol) of di-n-butyltin oxide and heated at 80° C. for 12 hours. After cooling to room temperature, the mixture is washed with saturated sodium bicarbonate solution. The organic phase is separated off, washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the filtrate is concentrated to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: dichloromethane→dichloromethane/methanol 10:1). 800 mg (1.4 mmol, 74% of theory) of a white foam are obtained.

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe mixture is washed with saturated sodium bicarbonate solution
  3. customThe organic phase is separated off
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated to dryness
  8. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: dichloromethane→dichloromethane/methanol 10:1)
  9. custom800 mg (1.4 mmol, 74% of theory) of a white foam are obtained

Sources & evidence

ORD record
ord-39b56e2928de4d55b97f8d7dd9eaf096
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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