Gamma-Butyrolactone → HCID 14051180, compound

HRID 1199707Notes

Reaction equation

HRID 1199707 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)/[CH:5]=[CH:6]/[C:7]1[S:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.CCCCCC.C([Li])CCC.[C:30]1(=[O:35])[O:34][CH2:33][CH2:32][CH2:31]1>O1CCCC1>[OH:35][CH2:30][CH2:31][CH2:32][C:33]([NH:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)/[CH:5]=[CH:6]/[C:7]1[S:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:34]

Participants

6

Reactant 4

HCID 7302Gamma-ButyrolactoneHCID 8058HexaneHCID 14051212HCID 14051212, compoundHCID 178418339Butyllithium

Product 1

HCID 14051180HCID 14051180, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 1.0 g of 2-(trans-3-aminostyryl)benzothiazole dissolved in 15 ml of anhydrous tetrahydrofuran was cooled to -78° C. and 2.8 ml of a n-hexane solution (1.55M) of n-butyl lithium was added dropwise in a nitrogen gas atmosphere. After a mixture was stirred at the same temperature for 25 minutes, 375 mg of γ-butyrolactone was injected, followed by stirring for 1 hour. After completion of the reaction, the mixture was extracted with ethyl acetate, dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The crude crystals obtained were washed with ethyl ether and dried to obtain 160 mg (yield 12%) of the title compound.

Workup

  1. stirringby stirring for 1 hour
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe crude crystals obtained
  7. washwere washed with ethyl ether
  8. customdried

Sources & evidence

ORD record
ord-5403b0668e1340f8835dfdfb833b381e
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

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