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Trimethylsilyldiazomethane → (5-(Methoxycarbonyl)furan-2-YL)boronic acid

HRID 1508491
Notes
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Reaction equation

HRID 1508491 reaction equation
[OH:1][B:2]([OH:11])[C:3]1[O:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1.[CH3:12][Si](C=[N+]=[N-])(C)C>C(Cl)Cl.CO>[CH3:12][O:9][C:8]([C:6]1[O:7][C:3]([B:2]([OH:1])[OH:11])=[CH:4][CH:5]=1)=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 166417445-Boronofuran-2-carboxylic acid

Product 1

HCID 12163655(5-(Methoxycarbonyl)furan-2-YL)boronic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-(Dihydroxyboryl)-2-furoic acid (200 mg, 1.283 mmol) was dissolved in CH2Cl2 (5 mL) and MeOH (0.556 mL). Trimethylsilyldiazomethane (1.283 mL, 2.57 mmol) was added dropwise. After 45 min, the reaction was quenched with AcOH dropwise until the yellow color disappeared. The reaction was concentrated in vacuo to give [5-(methoxycarbonyl)-2-furyl]boronic acid. 1H NMR (500 MHz, CD3OD): δ 7.20 (d, J=3.5 Hz, 1H); 7.05 (d, J=3.6 Hz, 1H); 3.87 (s, 3H).

Workup

  1. customthe reaction was quenched with AcOH dropwise until the yellow color
  2. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-1b41a39b4e1449f395f6ec3450c06de5
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09221834B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes