Methyl 3-hydroxypivalate → Methyl 2,2-dimethyl-3-oxopropanoate

HRID 538875

반응식

HRID 538875 반응식
[OH:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH3:8][C:3]([CH3:9])([CH:2]=[O:1])[C:4]([O:6][CH3:7])=[O:5]

참가 물질

4

반응물 2

HCID 84152Methyl 3-hydroxypivalateHCID 178418287HCID 178418287, 화합물

생성물 1

HCID 11137194Methyl 2,2-dimethyl-3-oxopropanoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Step-1: A solution of methyl 3-hydroxy-2,2-dimethylpropanoate (8.6 g, 65.1 mmol) in 100 mL DCM was cooled to 0° C. under N2. PCC (24.8 g, 115.2 mmol) was added portionwise over several minutes. The mixture was allowed to gradually warm to room temperature and was stirred overnight. The mixture was filtered through silica gel. Enough Celite is added to the remaining oil so that all is adsorbed. This is added to the top of a silica pad and this is washed with about 1.5 L DCM. The solution is then carefully concentrated in vacuo, maintaining the water bath at about 30° C. to obtain methyl 2,2-dimethyl-3-oxopropanoate as a clear colorless oil. 1H (300 MHz, CDCl3, δ) 9.60 (s, 1H), 3.70 (s, 3H), 1.29 (s, 6H).

후처리

  1. filtrationThe mixture was filtered through silica gel
  2. additionEnough Celite is added to the remaining oil so that
  3. additionThis is added to the top of a silica pad
  4. washthis is washed with about 1.5 L DCM
  5. concentrationThe solution is then carefully concentrated in vacuo
  6. temperaturemaintaining the water bath at about 30° C.

출처 및 근거

ORD 기록
ord-39a6386595774a3aa4b6cda8cb9f1c92
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865752B2

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