Potassium Carbonate → 3-Ethyl-2-hydroxyvaleric acid, 4-methoxybenzyl ester

HRID 1068243Notes

Reaction equation

HRID 1068243 reaction equation
[CH2:1]([CH:3]([CH2:9][CH3:10])[CH:4]([OH:8])[C:5]([OH:7])=[O:6])[CH3:2].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([CH:3]([CH2:9][CH3:10])[CH:4]([OH:8])[C:5]([O:7][CH2:17][C:16]1[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=1)=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 225947313-ethyl-2-hydroxyPentanoic acid

Product 1

HCID 572601153-Ethyl-2-hydroxyvaleric acid, 4-methoxybenzyl esterYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.2 g (8.2 mmol) of 3-ethyl-2-hydroxyvaleric acid (step A) in 15 mL of dry DMF, 1.4 mL (9.6 mmol) of 4-methoxybenzyl chloride and 1.3 g (9.4 mmol) of K2CO3 were added. After stirring the reaction overnight, it was partitioned between Et2O and water. The aqueous layer was extracted with Et2O. The combined organic layer was washed with water, brine, dried and concentrated. The residue was purified on a flash column using a gradient of 10-30% EtOAc in hexane to obtain 2.1 g of the desired product. 1H NMR (CDCl3) 0.84 (t, 3H), 0.96 (t, 3H), 1.2-1.6 (m, 5H), 2.67 (d, 1H), 3.83 (s, 3H), 4.27 (dd, 1H), 5.17 (ABq, 2H), 6.91(m, 2H), 7.31 (m, 2H).

Workup

  1. customthe reaction overnight, it
  2. customwas partitioned between Et2O and water
  3. extractionThe aqueous layer was extracted with Et2O
  4. washThe combined organic layer was washed with water, brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified on a flash column

Sources & evidence

ORD record
ord-42ddf90b0a0441e9a05a8ce02afa6a71
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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