Hydrochloric Acid → 2-Benzyloxyacetyl-gamma-butyrolactone

HRID 1586059Notes

Reaction equation

HRID 1586059 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[C:13]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14]1.[CH2:19]([O:26][CH2:27][C:28](OCC)=[O:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>O1CCCC1.C(OCC)(=O)C.CCCCCC>[CH2:19]([O:26][CH2:27][C:28]([CH:14]1[CH2:15][CH2:16][O:17][C:13]1=[O:18])=[O:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7302Gamma-ButyrolactoneHCID 7912DiisopropylamineHCID 290299Ethyl 2-(benzyloxy)acetateHCID 178418339Butyllithium

Product 1

HCID 114020542-Benzyloxyacetyl-gamma-butyrolactoneYield 87.2%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 10.6 ml of diisopropylamine in 75 ml of tetrahydrofuran was chilled to -70° C., and 46 ml of a 1.6N hexane solution of n-butyllithium were added dropwise to the solution. After completion of the addition, the mixture was stirred for 15 minutes, and a solution of 54.8 g of γ-butyrolactone in 50 ml of tetrahydrofuran was added dropwise over 55 minutes, and the mixture was stirred for 50 minutes. Further, a solution of 14.75 g of ethyl benzyloxyacetate in 50 ml of tetrahydrofuran was added, and the resultant mixture was stirred for 2.5 hours at -60 to -50° C. 5N hydrochloric acid was then added so as not to exceed 20° C. to adjust the pH of the mixture to 1-2. Ethyl acetate was added to the reaction system, and the resultant mixture was washed with a saturated saline solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The thus-obtained crude product was subjected to column chromatography on silica gel (elution solvent: hexane:ethyl acetate=3:1→2:1→1:1) to obtain 13.01 g (yield: 87.2%) of the intended product as a colorless oil.

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was stirred for 50 minutes
  3. customto exceed 20° C.
  4. washthe resultant mixture was washed with a saturated saline solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe thus-obtained crude product

Sources & evidence

ORD record
ord-d411f76602c44f4a88dd62127d4b1efb
Source dataset
uspto-grants-1999_08
Patent number
US05942515

Reaction notes

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