Sodium cyanoborohydride → 4-Hydroxy-5-hydroxymethyl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

HRID 29428ノート

反応式

HRID 29428 の反応式
[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([CH:18]=[O:19])=[C:14]([OH:20])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+]>C1COCC1>[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=[C:14]([OH:20])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 5003444Sodium cyanoborohydrideHCID 865990315-Formyl-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

生成物 1

HCID 687148834-Hydroxy-5-hydroxymethyl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester収率 46.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 5-formyl-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester (430 mg, 1.56 mmol) was added 8 mL of THF, followed by sodium cyanoborohydride (117 mg, 1.87 mmol) in one portion. The solution was stirred at room temperature for 1 h and then placed in a 65° C. oil bath overnight. The solvent was removed under vacuum and water was added. The mixture was extracted with ethyl acetate. Removal of the solvent gave the crude product, which was purified by column chromatography to give 200 mg of 4-hydroxy-5-hydroxymethyl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester was obtained as a yellow semi-solid.

後処理

  1. customplaced in a 65° C.
  2. customovernight
  3. customThe solvent was removed under vacuum and water
  4. additionwas added
  5. extractionThe mixture was extracted with ethyl acetate
  6. customRemoval of the solvent
  7. customgave the crude product, which
  8. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-72639567ca744487a982e8df8a237384
出典データセット
uspto-grants-2008_09
特許番号
US07420001B2

反応ノート

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