Ethanol → 3-(4-Hydroxy-benzyl)-3-methyl-pent-4-enoic Acid Ethyl Ester

HRID 1860684Notes

Reaction equation

HRID 1860684 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=1)([CH3:9])[CH:7]=[CH2:8])[CH3:2].B(Br)(Br)Br.C(O)C>ClCCl>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)([CH3:9])[CH:7]=[CH2:8])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 25134Boron tribromideHCID 22978426HCID 22978426, compound

Product 1

HCID 600748153-(4-Hydroxy-benzyl)-3-methyl-pent-4-enoic Acid Ethyl EsterYield 42.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product of STEP 4 (0.79 g) and dichloromethane (15 ml) was cooled to 0° C. A 1 M solution of boron tribromide in dichloromethane (6.00 ml) was added slowly. The solution was stirred at room temperature for 1 hour. Ethanol (5 ml) was added to quench the reaction. Solvent was removed. Residue was extracted with 1% of hydrochloric acid aqueous solution and ethyl acetate. The organic extract was washed with saturated sodium bicarbonate/water, and then dried over MgSO4. Solvent was removed. The crude product was purified on a silica gel column, eluting with 20% ethyl acetate/hexane to afford colorless oil (0.32 g). The 1H NMR was consistent with the proposed structure.

Workup

  1. customto quench
  2. customthe reaction
  3. customSolvent was removed
  4. extractionResidue was extracted with 1% of hydrochloric acid aqueous solution and ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with saturated sodium bicarbonate/water
  7. dry with materialdried over MgSO4
  8. customSolvent was removed
  9. customThe crude product was purified on a silica gel column
  10. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-16005c03f89b4a5f8fb122433d832036
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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