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

HRID 29428노트

반응식

HRID 29428 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-72639567ca744487a982e8df8a237384
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420001B2

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