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Dibutyltin oxide → HCID 178460975, compound

HRID 1921897
Notes
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Reaction equation

HRID 1921897 reaction equation
[C:1]([C:5]1[CH:51]=[CH:50][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]([CH2:30][C:31]2[CH:36]=[C:35]([F:37])[C:34]([O:38][Si:39]([CH:46]([CH3:48])[CH3:47])([CH:43]([CH3:45])[CH3:44])[CH:40]([CH3:42])[CH3:41])=[C:33]([F:49])[CH:32]=2)[CH2:20][CH2:21][C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N:56]=[N+:57]=[N-:58])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[CH:7][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]([CH2:30][C:31]2[CH:32]=[C:33]([F:49])[C:34]([O:38][Si:39]([CH:40]([CH3:42])[CH3:41])([CH:43]([CH3:44])[CH3:45])[CH:46]([CH3:48])[CH3:47])=[C:35]([F:37])[CH:36]=2)[CH2:20][CH2:21][C:22]2[CH:29]=[CH:28][C:25]([C:26]3[NH:58][N:57]=[N:56][N:27]=3)=[CH:24][CH:23]=2)=[CH:50][CH:51]=1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 57971908E-4-[5-[2-(4-tert-Butylbenzyloxy)phenyl]-3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)pent-4-enyl]benzonitrile

Product 1

HCID 178460975HCID 178460975, compound

Reagents, catalysts & solvents 1

HCID 1140Toluene
Solvent

Conditions

Temperature
80 °C

Procedure

A solution of 625 mg (85% pure, 0.75 mmol) of E-4-[5-[2-(4-tert-butylbenzyloxy)phenyl]-3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)pent-4-enyl]benzonitrile in 12 ml of toluene is mixed with 1.76 ml (13.24 mmol) of trimethylsilyl azide and 329.6 mg (1.3 mmol) of di-n-butyltin oxide and stirred at 80° C. for 12 h. After conversion is complete, the mixture is extracted with sodium bicarbonate solution. The aqueous phase is back-extracted twice with ethyl acetate. The combined organic phases are washed with sodium chloride solution, dried over sodium sulfate and concentrated. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:2→ethyl acetate). 447.3 mg (0.51 mmol, 86% purity, 58% of theory) of the title compound are obtained.

Workup

  1. extractionthe mixture is extracted with sodium bicarbonate solution
  2. extractionThe aqueous phase is back-extracted twice with ethyl acetate
  3. washThe combined organic phases are washed with sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:2→ethyl acetate)

Sources & evidence

ORD record
ord-8d834509c16e48ed954db95eca912a6b
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08173704B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes