Gamma-Butyrolactone → HCID 67190127, compound

HRID 546347Notes

Reaction equation

HRID 546347 reaction equation
[C:1]1(=[O:6])[O:5][CH2:4][CH2:3][CH2:2]1.[O:7]1[CH2:12][CH2:11][CH2:10][O:9][CH:8]1[CH2:13][CH2:14][Mg]Br.[O:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.[Cl-].[NH4+]>O1CCCC1>[O:7]1[CH2:12][CH2:11][CH2:10][O:9][CH:8]1[CH2:13][CH2:14][C:4]([CH2:3][CH2:2][CH:1]1[O:6][CH2:2][CH2:3][CH2:4][O:5]1)([OH:5])[CH2:18][CH2:19][CH2:20][CH2:21][OH:17]

Participants

5

Reactant 3

HCID 7302Gamma-ButyrolactoneHCID 25517Ammonium ChlorideHCID 178420633HCID 178420633, compound

Product 1

HCID 67190127HCID 67190127, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

430 mg (5 mmol) of γ-butyrolactone was dissolved in 10 ml of tetrahydrofuran, and 22 ml (11 mmol) of 0.5 M (1,3-dioxan-2-ylethyl)magnesium bromide/tetrahydrofuran solution was added thereto with stirring under ice-cooling, followed by stirring for 3 hours at 50° C. After the reaction solution was cooled with ice, saturated aqueous ammonium chloride was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; ethyl acetate:ethanol=10:1) to give 880 mg of the title compound as a colorless oil (yield: 55%).

Workup

  1. temperaturecooling
  2. stirringby stirring for 3 hours at 50° C
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-4810454f911443d1b7213f6f5ac0aa1c
Source dataset
uspto-grants-2011_05
Patent number
US07935835B2

Reaction notes

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