Benzyl Bromide → methyl 3-(benzyloxy)-2-thiophenecarboxylate

HRID 412227ノート

反応式

HRID 412227 の反応式
[OH:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:11]([O:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5811273-Hydroxy-thiophene-2-carboxylic acid methyl ester

生成物 1

HCID 2764114methyl 3-(benzyloxy)-2-thiophenecarboxylate収率 100.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of methyl 3-hydroxy-2-thiophenecarboxylate (5.00 g, 31.61 mmol), benzyl bromide (3.76 mL, 31.61 mmol), and K2CO3 (4.81 g, 34.77 g) in acetone (50 mL) was stirred at reflux for 1.5 hrs. After cooled to room temperature, the mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=15/1 to 9/1) to give methyl 3-(benzyloxy)-2-thiophenecarboxylate as a pale yellow oil (7.91 g, yield: quant.).

後処理

  1. temperatureat reflux for 1.5 hrs
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=15/1 to 9/1)

出典と根拠

ORDレコード
ord-75cf4f4eec564476b9452795719d4ce0
出典データセット
uspto-grants-2003_05
特許番号
US06562811B1

反応ノート

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