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Tributylvinyltin → HCID 67517397, compound

HRID 2173441
Notes
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Reaction equation

HRID 2173441 reaction equation
Br[C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[N:11][N:10]=[N:9]2)[CH:5]=[CH:4][C:3]=1[CH2:13][C:14]([OH:16])=[O:15].[Li+].[Cl-].[CH2:19]=[CH:20][Sn](CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:19]([C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[N:11][N:10]=[N:9]2)[CH:5]=[CH:4][C:3]=1[CH2:13][C:14]([OH:16])=[O:15])=[CH2:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 67517645HCID 67517645, compound

Product 1

HCID 67517397HCID 67517397, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst
HCID 1140
Toluene
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [2-bromo-4-(1H-tetrazol-1-yl)phenyl]acetic acid (100 mg, 0.35 mmol) in 10 mL of toluene was added LiCl (44 mg, 1.05 mmol), Pd(PPh3)4(10 mg), CH2═CHSnBu3 (222 mg, 0.7 mmol), and the mixture was heated to reflux overnight. After the reaction was completed, the reaction solution was diluted with EtOAc and filtered. The filtrate was concentrated and purified by prep-TLC to give [2-ethenyl-4-(1H-tetrazol-1-yl)phenyl]acetic acid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by prep-TLC

Sources & evidence

ORD record
ord-1e09d4bde36d4e618ce26b2e6535bb1f
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09056859B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes