Carbon Dioxide → HCID 18509459, compound

HRID 1356809Notes

Reaction equation

HRID 1356809 reaction equation
[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:16]=[C:15](Br)[CH:14]=[CH:13][C:12]=1[CH3:18])[CH3:9].C(=O)=[O:22].[CH2:24]([Li])[CH2:25][CH2:26]C.CCCCCC.[Cl-].[NH4+]>O1CCCC1.CC(C)=O>[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:16]=[C:15]([C:25]([OH:22])([CH3:26])[CH3:24])[CH:14]=[CH:13][C:12]=1[CH3:18])[CH3:9]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 18509519HCID 18509519, compoundHCID 178418339Butyllithium

Product 1

HCID 18509459HCID 18509459, compoundYield 50.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Compound 32 (1.10 g) was dissolved in tetrahydrofuran (10 ml), and the solution was cooled to −78° C. by use of a mixture of dry ice and acetone solvent. n-butyl lithium in n-hexane (1.63 M: 2.1 ml; 1.04 eq) was slowly added dropwise to the mixture, and stirred for 5 minutes, followed by dropwise addition of acetone (290 μl; 1.2 eq). The mixture was stirred for 15 minutes, and gradually brought to room temperature. Saturated aqueous ammonium chloride solution was added dropwise to the mixture, and the reaction was stopped, followed by extraction with ether (120 ml). The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane ethyl acetate=5:1), to thereby yield 520 mg of the target compound (yield: 50.4%).

Workup

  1. stirringThe mixture was stirred for 15 minutes
  2. customgradually brought to room temperature
  3. extractionfollowed by extraction with ether (120 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane ethyl acetate=5:1)

Sources & evidence

ORD record
ord-15d24c5c6da54940b6424bde7915f0dc
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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