Potassium Iodide → Methyl 2-(4-(3-(tert-butyldimethylsilyloxy)propoxy)-2-methoxybenzyl)-3-oxobutanoate

HRID 2207083노트

반응식

HRID 2207083 반응식
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[C:11]([Si:15]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]Cl)=[C:25]([O:31][CH3:32])[CH:24]=1)([CH3:17])[CH3:16])([CH3:14])([CH3:13])[CH3:12].[I-].[K+]>CN(C=O)C.O>[Si:15]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH3:8])=[O:6])=[C:25]([O:31][CH3:32])[CH:24]=1)([C:11]([CH3:13])([CH3:12])[CH3:14])([CH3:16])[CH3:17]

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 123781615Tert-butyl {3-[4-(chloromethyl)-3-methoxyphenoxy]propoxy}dimethylsilane

생성물 1

HCID 68752908Methyl 2-(4-(3-(tert-butyldimethylsilyloxy)propoxy)-2-methoxybenzyl)-3-oxobutanoate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

Methyl acetoacetate (4.18 mL) was added to a suspension of NaH (55% oil dispersion, 1.70 g) in DMF (60 mL) at 0° C. and stirred at r.t. for 0.5 h. The product from step (iii) (10.0 g) in DMF (60 mL) and potassium iodide (4.73 g) were added to the mixture and stirred at 80° C. for 6 h. The mixture was cooled to RT and diluted with water and extracted with EtOAc. And the combined organic solutions were washed with water and brine, dried and concentrated. The residue was purified by silica gel chromatography to give 9.98 g of the subtitle compound as a yellow oil; 1H NMR: 6.99 (1H, d), 6.42 (1H, d), 6.37 (1H, dd), 4.02 (2H, t), 3.89 (1H, t), 3.80 (3H, s), 3.79 (2H, t), 3.67 (3H, s), 2.99-3.14 (2H, m), 2.17 (3H, s), 1.92-2.00 (2H, m), 0.88 (9H, s), 0.04 (6H, s).

후처리

  1. stirringstirred at 80° C. for 6 h
  2. temperatureThe mixture was cooled to RT
  3. extractionextracted with EtOAc
  4. washAnd the combined organic solutions were washed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-ee5d7cc014a940c09a52001631c54ab1
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376398B2

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