HCID 12017160, compound → HCID 12017161, compound

HRID 277882Notes

Reaction equation

HRID 277882 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[CH2:18][CH2:17][CH:16]([CH2:19][C:20]([CH3:22])=[CH2:21])[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]1[CH2:18][CH2:17][CH:16]([CH2:19][C:20]([CH3:22])=[CH2:21])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 12017160HCID 12017160, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12017161HCID 12017161, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of LAH (17 mg, 0.44 mmol) in THF (2 mL) at reflux was added 1-3 (100 mg, 0.44 mmol) in THF (1 mL) dropwise over a 5 min period. The reaction mixture was then maintained at reflux for an additional 12 hrs and then quenched sequentially with H2O (17 μL), 15% NaOH (17 μL), and H2O (51 μL). After 10 min, MgSO4 was added followed by filtration and concentration of the filtrate to give 1-4 as a yellow oil.

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture was then maintained
  3. temperatureat reflux for an additional 12 hrs
  4. customquenched sequentially with H2O (17 μL), 15% NaOH (17 μL), and H2O (51 μL)
  5. additionMgSO4 was added
  6. filtrationfollowed by filtration and concentration of the filtrate

Sources & evidence

ORD record
ord-9bfa4d1b447d4a6ea840b47227581c6c
Source dataset
uspto-grants-2002_03
Patent number
US06358970B1

Reaction notes

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