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

HRID 374482

反応式

HRID 374482 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 7037498(R)-(-)-4-(oxiranylmethoxy)-benzaldehyde収率 89.1%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-0142865354294b02b38cff5746f2279e
出典データセット
uspto-grants-1996_01
特許番号
US05480899

関連ノート

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