Benzyl Alcohol → Ethyl 4-(benzyloxy)-3-oxobutanoate

HRID 1586031Notes

Reaction equation

HRID 1586031 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:12][C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C1COCC1>[CH2:3]([O:10][CH2:12][C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 9813448Ethyl 4-(benzyloxy)-3-oxobutanoateYield 150,933%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of NaH (3 g, 0.1 mmol, 80% oil dispersion previously washed with hexanes), in THF (75 ml, distilled from Na) was added dropwise neat benzyl alcohol (10.3 g. 0.1 mmol) at rt. Stirring was continued until H2 evolution had ceased, then ethyl 4-chloroacetoacetate (8.23 g, 0.05 mmol) in THF (20 ml) was added dropwise to this solution in a cooling water bath. The reaction was stirred at rt overnight. The mixture was partitioned between ether and 1 N HCl, the layers separated, and the aqueous further extracted with ether (×2). The combined ether extracts were washed twice with water and then brine and dried (Na2SO4), filtered, and concentrated in vacuo to give 17.83 g crude product. Distillation (119-124° C., 0.2 mm Hg) afforded a yellow oil. (7.34 g, 62%)

Workup

  1. washpreviously washed with hexanes), in THF (75 ml, distilled from Na)
  2. stirringThe reaction was stirred at rt overnight
  3. customThe mixture was partitioned between ether and 1 N HCl
  4. customthe layers separated
  5. extractionthe aqueous further extracted with ether (×2)
  6. washThe combined ether extracts were washed twice with water
  7. dry with materialbrine and dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad38882019184fe38e1513f49181de73
Source dataset
uspto-grants-1999_08
Patent number
US05942516

Reaction notes

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