Trimethylsilyldiazomethane → Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-3-carboxylate

HRID 1508490Notes

Reaction equation

HRID 1508490 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([B:9]2[O:17][C:14]([CH3:16])([CH3:15])[C:11]([CH3:13])([CH3:12])[O:10]2)[O:7][CH:8]=1)([OH:3])=[O:2].[CH3:18][Si](C=[N+]=[N-])(C)C>C(Cl)Cl.CO>[CH3:12][C:11]1([CH3:13])[C:14]([CH3:16])([CH3:15])[O:17][B:9]([C:6]2[O:7][CH:8]=[C:4]([C:1]([O:3][CH3:18])=[O:2])[CH:5]=2)[O:10]1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 467390315-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-3-carboxylic acid

Product 1

HCID 53217215Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-3-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-Carboxyfuran-2-boronic acid pinacol ester (200 mg, 0.840 mmol) was dissolved in CH2Cl2 (4 mL) and MeOH (0.444 mL). Trimethylsilyldiazomethane (0.840 mL, 1.680 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 methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-furoate. 1H NMR (500 MHz, CDCl3): δ 8.20 (s, 1H); 7.37 (s, 1H); 3.84 (s, 3H); 1.36 (s, 12H).

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-5d3cca8ccf0940ba8a7653d6d5747f26
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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