Dibutyltin oxide → HCID 178497738, compound

HRID 1927398Notes

Reaction equation

HRID 1927398 reaction equation
[C:1]([C:5]1[CH:42]=[CH:41][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]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=2)[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N:47]=[N+:48]=[N-:49])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:42]=[CH:41][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]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[NH:49][N:48]=[N:47][N:40]=3)=[CH:35][CH:34]=2)[CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 57831375Methyl 4-{(3E)-4-{2-[(4-tert-butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}-benzoate

Product 1

HCID 178497738HCID 178497738, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1000 mg (1.79 mmol) of methyl 4-{(3E)-4-{2-[(4-tert-butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoate in 10 ml of toluene is mixed with 2851 mg (24.7 mmol) of trimethylsilyl azide and 618 mg (2.47 mmol) of di-n-butyltin oxide and heated at 80° C. for 12 h. 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 chromatography on a silica gel column (mobile phase: cyclohexane/ethyl acetate 2:1→1:2). 648 mg (1.08 mmol, 60% of theory) of a colorless oil 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 chromatography on a silica gel column (mobile phase: cyclohexane/ethyl acetate 2:1→1:2)
  9. custom648 mg (1.08 mmol, 60% of theory) of a colorless oil are obtained

Sources & evidence

ORD record
ord-7c203f23b9424b8f9014cc99f65ce0ab
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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