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

HRID 1508490ノート

反応式

HRID 1508490 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-5d3cca8ccf0940ba8a7653d6d5747f26
出典データセット
uspto-grants-2015_12
特許番号
US09221834B2

反応ノート

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