Hydrochloric Acid → HCID 18410368, compound

HRID 993361Notes

Reaction equation

HRID 993361 reaction equation
Br[CH2:2][CH2:3][C:4]([OH:6])=[O:5].C([Li])CCC.[CH:12]12[CH2:18][CH:15]([CH:16]=[CH:17]1)[CH2:14][CH:13]2[CH2:19][CH:20]=O.Cl>O1CCCC1.CN(C)P(=O)(N(C)C)N(C)C.CCCCCC>[CH:12]12[CH2:18][CH:15]([CH:16]=[CH:17]1)[CH2:14][CH:13]2[CH2:19][CH:20]1[O:6][C:4](=[O:5])[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 115533-Bromopropionic acidHCID 55627480376-88-1HCID 178418339Butyllithium

Product 1

HCID 18410368HCID 18410368, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
20 °C

Procedure

In 80 g of dry tetrahydrofuran was dissolved 10.0 g of 3-bromopropionic acid. In a nitrogen atmosphere, 85.0 g of a hexane solution of 1.6M n-butyllithium was added to the solution at −78° C., followed by 30 minutes of stirring. Then a solution of 8.92 g 2-(5-norbornen-2-yl)acetaldehyde in 20 g hexamethylphosphoric triamide was added dropwise to the solution at the same temperature. With stirring, the temperature of the solution was gradually raised to 20° C. over 2 hours. Next, 80 g of 5% hydrochloric acid was added to the solution, which was stirred for one hour for lactonization. The organic layer was separated, washed with aqueous saturated sodium bicarbonate solution, washed with water, and concentrated in vacuum. Purification by silica gel column chromatography yielded 8.17 g (yield 65%) of γ-(5-norbornen-2-yl)methyl-γ-butyrolactone. The analytical properties of this compound were substantially identical with the data of Synthesis Example 1.

Workup

  1. stirringWith stirring
  2. stirringwas stirred for one hour for lactonization
  3. customThe organic layer was separated
  4. washwashed with aqueous saturated sodium bicarbonate solution
  5. washwashed with water
  6. concentrationconcentrated in vacuum
  7. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-90cd41c0caf942cda727393e2ce38f43
Source dataset
uspto-grants-2002_10
Patent number
US06472543B2

Reaction notes

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