Water → 3-[Hydroxy(3-methoxyphenyl)methyl)-2-oxotetrahydrofuran

HRID 380086Notes

Reaction equation

HRID 380086 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH:9](=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1.[C:19]([O:22][CH2:23][CH3:24])(=[O:21])[CH3:20].O>O1CCCC1>[OH:18][CH:9]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)[CH:20]1[CH2:24][CH2:23][O:22][C:19]1=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 115693-MethoxybenzaldehydeHCID 2724682Lithium diisopropylamide

Product 1

HCID 183672943-[Hydroxy(3-methoxyphenyl)methyl)-2-oxotetrahydrofuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of y-butyrolactone (3.0 g) in tetrahydrofuran (THF) (30 ml) was added lithium diisopropylamide (LDA) (28 ml, 1.5 M solution in cyclohexane) at −78° C. under N2, and then after 30 minutes, a solution of m-anisaldehyde (4.7 g) in THF (10 ml) was added in the solution. After being stirred for 2 hours at the same temperature, the solution was poured into the mixture of ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 3-[hydroxy(3-methoxyphenyl)methyl)-2-oxotetrahydrofuran (7.4 g).

Workup

  1. washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b267b7cd89aa48ec92b81d806e93f97a
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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