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

HRID 1494110
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인쇄 미리보기

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HRID 1494110 반응식
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]
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참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 14986673Methyl 2,2-dimethyl-4-(2-hydroxyethyl)-8-(t-butyldimethylsiloxy)octanoate

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-64eea7e9683e44d1999c9c47dda55ea3
출처 데이터셋
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05025025

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