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

HRID 2207083ノート

反応式

HRID 2207083 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ee5d7cc014a940c09a52001631c54ab1
出典データセット
uspto-grants-2016_06
特許番号
US09376398B2

反応ノート

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