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Dibutyltin oxide → HCID 178471345, compound

HRID 1927436
Notes
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Reaction equation

HRID 1927436 reaction equation
[C:1]([C:5]1[CH:40]=[CH:39][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][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=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:45]=[N+:46]=[N-:47])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:40]=[CH:39][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][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]3[NH:47][N:46]=[N:45][N:38]=3)=[CH:33][CH:32]=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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 57831336HCID 57831336, compound

Product 1

HCID 178471345HCID 178471345, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1 g (1.86 mmol) of ethyl (7E)-8-{2-[(4-tert-butylbenzyl)oxy]phenyl}-6-[2-(4-cyanophenyl)ethyl]-oct-7-enoate in 70 ml of toluene is mixed with 3.7 ml (27.9 mmol) of trimethylsilyl azide and 694 mg (2.79 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: cyclohexane/ethyl acetate 4:1→1:1). 622 mg (1.1 mmol, 34% 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: cyclohexane/ethyl acetate 4:1→1:1)
  9. custom622 mg (1.1 mmol, 34% of theory) of a white foam are obtained

Sources & evidence

ORD record
ord-addd199f97ea4d128f68c732dbdca991
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08183271B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes