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Triethylamine → Methyl (S)-2-methyl-3-((methylsulfonyl)oxy)propanoate

HRID 258483
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HRID 258483 반응식
[OH:1][CH2:2][C@H:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5].[CH3:9][S:10](Cl)(=[O:12])=[O:11].CCN(CC)CC>C(Cl)Cl>[CH3:9][S:10]([O:1][CH2:2][C@H:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5])(=[O:12])=[O:11]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10192563methyl (2S)-3-hydroxy-2-methylpropanoate

생성물 1

HCID 11608092Methyl (S)-2-methyl-3-((methylsulfonyl)oxy)propanoate수율 102.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of methyl 3-hydroxy-2-(S)-methylpropanoate (35 g, 295 mmol) in 830 mL of CH2Cl2, under N2 atmosphere, was cooled to -60° C. With rapid stirring, methanesulfonyl chloride (24 mL, 310 mmol) was added, followed by Et3N (50 mL, 354 mmol) over 90 s. As the addition ended, a heavy white precipitate formed which stopped the magnetic stirring. The cold bath was removed and the reaction allowed to reach r.t. The reaction mixture was poured into aq 25% NH4OAc. After separation, the organic phase was dried over MgSO4 and evaporated to give the title compound as a colorless oil (59.1 g, 102%).

후처리

  1. additionAs the addition
  2. customa heavy white precipitate formed which
  3. customThe cold bath was removed
  4. customto reach r.t
  5. additionThe reaction mixture was poured into aq 25% NH4OAc
  6. customAfter separation
  7. dry with materialthe organic phase was dried over MgSO4
  8. customevaporated

출처 및 근거

ORD 기록
ord-1c77de2087dd4de8848a021796489ba1
출처 데이터셋
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05266568

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