4-Hydroxybenzaldehyde → (R)-(-)-4-(oxiranylmethoxy)-benzaldehyde

HRID 374482

반응식

HRID 374482 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[N+](C1C=C(S(O[CH2:23][C@@H:24]2[O:26][CH2:25]2)(=O)=O)C=CC=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[O:26]1[CH2:25][C@@H:24]1[CH2:23][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl ester

생성물 1

HCID 7037498(R)-(-)-4-(oxiranylmethoxy)-benzaldehyde수율 89.1%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

In 800 ml of anhydrous methyl ethyl ketone was dissolved 23.54 g of 4-hydroxybenzaldehyde and 50 g of (R)-(-)-glycidyl m-nitrobenzenesulfonate. To the solution was added 34.6 g of anhydrous potassium carbonate, and the mixture was refluxed with heating for 2.5 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was extracted with ethyl acetate. The extract was washed with water, dried with magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and purified with chloroform to give 30.6 g of the title compound (yield 89%).

후처리

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 2.5 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. extractionThe obtained residue was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. custompurified with chloroform

출처 및 근거

ORD 기록
ord-0142865354294b02b38cff5746f2279e
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05480899

연결된 노트

불러오는 중…