Dimethylformamide → 2-(3,6-dihydro-2H-pyran-4-yl)-2-methyl-propionic acid ethyl ester

HRID 1807045노트

반응식

HRID 1807045 반응식
[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:8]1(O)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)([CH3:7])[CH3:6])[CH3:2].S(Cl)(Cl)=O.CN(C)C=O>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:8]1[CH2:13][CH2:12][O:11][CH2:10][CH:9]=1)([CH3:7])[CH3:6])[CH3:2]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 62399213Ethyl tetrahydro-4-hydroxy-alpha,alpha-dimethyl-2H-pyran-4-acetate

생성물 1

HCID 672969602-(3,6-dihydro-2H-pyran-4-yl)-2-methyl-propionic acid ethyl ester수율 99%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
100 °C

실험 절차

Step B To a solution of 2-(4-hydroxy-tetrahydro-pyran-4-yl)-2-methyl-propionic acid ethyl ester (19.5 g, 90 mmol) in chloroform (100 mL) was added thionyl chloride (13.3 mL, 180 mmol) and dimethylformamide (0.28 mL). The reaction mixture was heated at 100° C. for 18 h, then cooled to room temperature and concentrated. To the resulting residue was added aqueous NaOH solution (10 N) to adjust the “pH” of the mixture to basic. The mixture was then extracted with ethyl acetate twice. The combined organic extracts were washed with water, brine, dried over MgSO4, and concentrated to give 2-(3,6-dihydro-2H-pyran-4-yl)-2-methyl-propionic acid ethyl ester as a brown oil (17.6 g, 99%).

후처리

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. additionTo the resulting residue was added aqueous NaOH solution (10 N)
  4. extractionThe mixture was then extracted with ethyl acetate twice
  5. washThe combined organic extracts were washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9df3eba99a684c4dbeab313e340eaa4d
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354444B2

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