Aluminium lithium hydride → HCID 54233292, compound

HRID 842048Notes

Reaction equation

HRID 842048 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:28])=[CH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:16]([O:23][CH2:24][C:25](O)=[O:26])=[CH:15][CH:14]=2)[N:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][C:2]1[NH:3][C:4]([CH3:28])=[CH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:16]([O:23][CH2:24][CH2:25][OH:26])=[CH:15][CH:14]=2)[N:8]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54354393HCID 54354393, compound

Product 1

HCID 54233292HCID 54233292, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 100 mL round-bottomed flask equipped with condenser and nitrogen (N2) inlet were added 100 mg (0.27 mmol) 2-(2,5-dimethylpyrrolyl)6-[4-carboxymethoxy-5,6,7,8-tetrahydro-naphthalen-1-yl]-pyridine (from Example 1), 20 mL dry tetrahydrofuran, and 0.6 mL (0.53 mmol) of a 1 M solution of lithium aluminum hydride in tetrahydrofuran. The reaction was refluxed 16 hour, cooled, and quenched with 1 N hydrochloric acid. The mixture was adjusted to pH 10 with 1 N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue of 118 mg (100%), an oil, was used directly in the following step. 1H-NMR (δ, CDCl3): 1.69 (m, 2H), 1.78 (m, 2H), 2.16 (s, 6H), 2.7-2.9 (m, 4H), 3.95 (m, 2H), 4.08 (m, 2H), 5.885 (s, 2H), 6.73 (d, J=8, 1H), 7.13 (d, J=8, 1H), 7.20 (d, J=8, 1H), 7.35 (d, J=8, 1H), 7.83 (t, J=8, 1H); MS (%): 363 (parent+1, 100).

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and nitrogen (N2) inlet
  2. temperatureThe reaction was refluxed 16 hour
  3. temperaturecooled
  4. customquenched with 1 N hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-7d0849dd5f934647a0a3900fbd85f8b9
Source dataset
uspto-grants-2002_04
Patent number
US06372768B1

Reaction notes

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