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

HRID 2301693

Reaction equation

HRID 2301693 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8058HexaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7d6786bc9e194b04a280c19ded1b9c6b
Source dataset
uspto-grants-2002_12
Patent number
US06500961B2

Linked notes

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