4-Toluenesulfonyl chloride → (R)-Methyl 2-(p-Tolyloxy)propanoate

HRID 16115

반응식

HRID 16115 반응식
[C:1]([O:6][CH3:7])(=[O:5])[C@@H:2]([CH3:4])[OH:3].C(N(CC)CC)C.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18](S(Cl)(=O)=O)=[CH:17][CH:16]=1>C(#N)C.Cl.CN(C)C>[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([O:3][C@H:2]([CH3:4])[C:1]([O:6][CH3:7])=[O:5])=[CH:17][CH:16]=1

참가 물질

6

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 637514(+)-Methyl lactate

생성물 1

HCID 1540374(R)-Methyl 2-(p-Tolyloxy)propanoate수율 116%

시약·촉매·용매 2

HCID 10313079Trimethylamine Hydrochloride촉매HCID 6342Acetonitrile용매2회

실험 절차

A solution of methyl (R)-(+)-lactate (6.66 g) in acetonitrile (33 ml) was cooled to 5° C. and triethylamine (9.8 ml) added followed by trimethylamine hydrochloride (0.62 g). A separate solution of p-toluenesulfonyl chloride (11.6 g) in acetonitrile (33 ml) was added dropwise over 20 mins maintaining the temperature below 5° C. The reaction mixture was filtered and concentrated. Diethyl ether and water were added and the organic fraction dried (MgSO4) and concentrated in vacuo to give the sub-title compound as a yellow oil (13.71 g).

후처리

  1. temperaturemaintaining the temperature below 5° C
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. additionDiethyl ether and water were added
  5. dry with materialthe organic fraction dried (MgSO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-19235ac9b2db47e3990438cc395213d9
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737135B2

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