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Dimethyl Sulfoxide → Methyl 2,2-dimethyl-4-(formylmethyl)-8-(t-butyldimethylsiloxy)octanoate

HRID 1494110
ノート
印刷プレビュー

反応式

HRID 1494110 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][C:12]([CH3:34])([CH2:17][CH:18]([CH2:31][CH2:32][OH:33])[CH2:19][CH2:20][CH2:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[C:13]([O:15][CH3:16])=[O:14].C(N(CC)CC)C>C(Cl)Cl>[CH3:11][C:12]([CH3:34])([CH2:17][CH:18]([CH2:31][CH:32]=[O:33])[CH2:19][CH2:20][CH2:21][CH2:22][O:23][Si:24]([C:27]([CH3:28])([CH3:29])[CH3:30])([CH3:26])[CH3:25])[C:13]([O:15][CH3:16])=[O:14]
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 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 14986673Methyl 2,2-dimethyl-4-(2-hydroxyethyl)-8-(t-butyldimethylsiloxy)octanoate

生成物 1

HCID 14986674Methyl 2,2-dimethyl-4-(formylmethyl)-8-(t-butyldimethylsiloxy)octanoate

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
3 回

実験手順

To a solution of 3.4 mL (48 mmol) dimethyl sulfoxide in 140 mL dry methylene chloride at -78° C. is added dropwise 3.0 mL (35 mmol) oxalyl chloride. The solution is stirred for 15 minutes and a solution of 2.57 g (7.1 mmol) methyl 2,2-dimethyl-4-(2-hydroxyethyl)-8-(t-butyldimethylsiloxy)octanoate in 20 mL dry methylene chloride is added slowly. The solution is stirred at -60° C. for 15 minutes and 15 mL (0.11 mole) triethylamine is added. The reaction is allowed to warm to room temperature and diluted with methylene chloride. The organic layer is washed with saturated aqueous sodium bicarbonate solution, water and brine. The organic phase is dried, filtered and concentrated to dryness. The oil is dissolved in ether and the solution is washed with water. The organic phase is dried, filtered and concentrated to give methyl 2,2-dimethyl-4-formylmethyl-8-(t-butyldimethylsiloxy)-octanoate; NMR (CDCl3) delta 9.8 (t,1H), 3.67 (s,3H), 1.2 (s,6H), 0.89 (s,9H).

後処理

  1. stirringThe solution is stirred at -60° C. for 15 minutes
  2. washThe organic layer is washed with saturated aqueous sodium bicarbonate solution, water and brine
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. dissolutionThe oil is dissolved in ether
  7. washthe solution is washed with water
  8. customThe organic phase is dried
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-64eea7e9683e44d1999c9c47dda55ea3
出典データセット
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05025025

反応ノート

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