Hydrochloric Acid → 3-[(Bicyclo[2.2.1]hept-5-en-2-yl)(hydroxy)methyl]oxolan-2-one

HRID 431414

반응식

HRID 431414 반응식
Br[CH:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4].[CH:8]12[CH2:14][CH:11]([CH:12]=[CH:13]1)[CH2:10][CH:9]2[CH:15]=[O:16].O1CCCC1.Cl>[Zn].CCCCCC>[OH:16][CH:15]([CH:9]1[CH2:10][CH:11]2[CH2:14][CH:8]1[CH:13]=[CH:12]2)[CH:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 95117Bicyclo(2.2.1)hept-5-ene-2-carboxaldehydeHCID 954632(3H)-Furanone, 3-bromodihydro-

생성물 1

HCID 183456893-[(Bicyclo[2.2.1]hept-5-en-2-yl)(hydroxy)methyl]oxolan-2-one수율 71.2%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8058Hexane용매

실험 절차

Addition reaction was carried out by mixing 98 g of zinc powder, 247 g of α-bromo-γ-butyrolactone, 122 g of 5-norbornene-2-carbaldehyde, and 2 kg of dry tetrahydrofuran and heating the mixture under reflux for 10 hours in a nitrogen atmosphere. The reaction mixture was cooled, to which dilute hydrochloric acid was added for neutralization and hexane was added for extraction. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuum. Purification by silica gel column chromatography yielded 148 g (yield 71%) of α-[hydroxy(5-norbornen-2-yl)methyl]-γ-butyrolactone.

후처리

  1. additionAddition reaction
  2. temperatureheating the mixture
  3. temperatureunder reflux for 10 hours in a nitrogen atmosphere
  4. additionwas added for extraction
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum
  9. customPurification by silica gel column chromatography

출처 및 근거

ORD 기록
ord-88b6649bad3446cd9463ae695dd1dc8e
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660448B2

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