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Triethylsilane → Dimethyl-3-(tetrahydro-furan-3-yloxy)-propionic acid methyl ester

HRID 1046443
ノート
印刷プレビュー

反応式

HRID 1046443 の反応式
[CH3:1][O:2][C:3](=[O:13])[C:4]([CH3:12])([CH3:11])[CH2:5][O:6][Si](C)(C)C.[O:14]1[CH2:18][CH2:17][C:16](=O)[CH2:15]1.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>[N+](C)([O-])=O>[CH3:1][O:2][C:3](=[O:13])[C:4]([CH3:12])([CH3:11])[CH2:5][O:6][CH:16]1[CH2:17][CH2:18][O:14][CH2:15]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 5293923-OxotetrahydrofuranHCID 866501662,2-Dimethyl-3-trimethylsilanyloxy-propionic acid methyl ester

生成物 1

HCID 58114071Dimethyl-3-(tetrahydro-furan-3-yloxy)-propionic acid methyl ester収率 89.5%

試薬・触媒・溶媒 1

HCID 6375
Nitromethane
溶媒

実験手順

2,2-Dimethyl-3-trimethylsilanyloxy-propionic acid methyl ester (478 mg, 2.34 mmol) was added to a solution of dihydro-furan-3-one (168 mg, 1.95 mmol) and FeCl3 (16 mg, 0.097 mmol) in nitromethane (6.0 mL) at 0° C. Triethylsilane (0.374 mL, 2.33 mmol) was added and the reaction was warmed to room temperature and stirred for 2 h. Sat. NaHCO3 was added and the reaction was extracted with dichloromethane. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated to give a pale liquid. Purification by flash column chromatography on silica gel using 30% ethyl acetate in hexanes provided dimethyl-3-(tetrahydro-furan-3-yloxy)-propionic acid methyl ester (353 mg, 75%) as a colorless liquid.

後処理

  1. extractionthe reaction was extracted with dichloromethane
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a pale liquid
  7. customPurification by flash column chromatography on silica gel using 30% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-6d5022cbbad94e489dcc14d88265b5b8
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08569302B2

反応ノート

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