Imidazole → Methyl 3-[4-(tert-butyldimethylsilyloxy)-3-oxobutyl]phenylacetate

HRID 278480노트

반응식

HRID 278480 반응식
[OH:1][CH2:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:10][CH:11]=1.N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C=O)C>[Si:23]([O:1][CH2:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:10][CH:11]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 22628477Methyl 3-(4-hydroxy-3-oxobutyl)phenylacetate

생성물 1

HCID 22628459Methyl 3-[4-(tert-butyldimethylsilyloxy)-3-oxobutyl]phenylacetate수율 94.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To an ice cooled solution of methyl 3-(4-hydroxy-3-oxo-butyl)phenylacetate (472 mg, 2.00 mmol) in DMF (10 ml) was added imidazole (264 mg, 3.88 mmol) followed by tert-butyldimethylsilyl chloride (408 mg, 5.99 mmol). After 30 minutes the ice-bath was removed and then the mixture was stirred overnight at room temperature. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried (magnesium sulfate), and concentrated in vacuo. The residue was purified by silica gel (20 g) column chromatography eluting with hexane/ethyl acetate (10:1) to give methyl 3-[4-(tert-butyldimethylsilyloxy)-3-oxobutyl]phenylacetate (664 mg, 94.9%) as a colorless oil.

후처리

  1. customAfter 30 minutes the ice-bath was removed
  2. additionThe reaction mixture was poured into water (100 ml)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel (20 g) column chromatography
  8. washeluting with hexane/ethyl acetate (10:1)

출처 및 근거

ORD 기록
ord-b774a9a2e1924066b5eae6f3b0d8fa73
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06359145B1

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