Tetrahydrofuran → HCID 18509401, compound

HRID 1356854Notes

Reaction equation

HRID 1356854 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:16]=[C:15]([C:17]([CH3:19])=[CH2:18])[CH:14]=[C:13](Br)[CH:12]=1)[CH3:9].[CH2:23]([Li])[CH2:24][CH2:25]C.CCCC[CH2:32][CH3:33].[Cl-].[NH4+].[O:36]1CCCC1>CC(C)=O>[C:17]([C:15]1[CH:14]=[C:13]([C:24]([OH:36])([CH3:23])[CH3:25])[CH:12]=[C:11]([CH2:10][N:8]([CH2:7][C:6]2[CH:33]=[CH:32][C:3]([C:2]([CH3:22])([CH3:21])[CH3:1])=[CH:4][CH:5]=2)[CH3:9])[CH:16]=1)([CH3:19])=[CH2:18]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 18509472HCID 18509472, compoundHCID 178418339Butyllithium

Product 1

HCID 18509401HCID 18509401, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
-78 °C

Procedure

Compound 67 (0.80 g; 2.07 mmol) was dissolved in tetrahydrofuran (15 ml). While the solution was stirred at −78° C. under nitrogen atmosphere, n-butyl lithium in n-hexane (1.63 M: 1.3 ml; 2.1 mmol) was slowly added dropwise. After 10 minutes, acetone (0.5 ml) was added dropwise thereto, and the mixture was gradually brought to room temperature. Reaction was stopped by dropwise addition of saturated aqueous ammonium chloride solution, and the mixture was extracted with diethyl ether (100 ml). The organic layer was washed with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→2:1), to thereby yield 0.28 g of the target compound (yield: 37.0%).

Workup

  1. customwas gradually brought to room temperature
  2. customReaction
  3. extractionthe mixture was extracted with diethyl ether (100 ml)
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→2:1)

Sources & evidence

ORD record
ord-59570d93202443748e6f0c56cf8ddd4e
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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