Aluminium lithium hydride → HCID 71735771, compound

HRID 1053554Notes

Reaction equation

HRID 1053554 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:11]1([NH:10][CH2:8][CH2:7][O:6][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:18][CH:17]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21335871HCID 21335871, compound

Product 1

HCID 71735771HCID 71735771, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 1b (1.5 g, 6.1 mmol) was dissolved in anhydrous THF (50 mL). LiAlH4 (500 mg, 13 mmol) was added to the mixture under argon. The reaction mixture was heated to reflux for 4 hr. After cooling to room temperature, the reaction was carefully quenched with water (50 mL). The mixture was adjusted pH to ˜7 with diluted hydrochloric acid. The mixture was then extracted with EtOAc and the combined organic layer was washed with water and then brine and dried over Na2SO4. The solvent was evaporated and the residue was purified by flash chromatography on silica gel to provide the product compound 1 (190 mg, 0.83 mmol, 14% yield) as a pale-yellow powder. HRMS (ESI, positive) m/z calcd. for C14H16NO2 [M+H]+: 230.1181, found: 230.1190; m/z calcd. for C14H15NO2Na [M+Na]+: 252.1001, found: 251.1061. 1H NMR (CDCl3, 400 MHz) δ 7.25 (t, J=8.6 Hz, 2H), 6.83-6.76 (m, 5H), 6.71 (d, J=7.2 Hz, 2H), 4.12 (t, J=5.0 Hz, 2H), 3.52 (t, J=5.0 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hr
  3. customthe reaction was carefully quenched with water (50 mL)
  4. extractionThe mixture was then extracted with EtOAc
  5. washthe combined organic layer was washed with water
  6. dry with materialbrine and dried over Na2SO4
  7. customThe solvent was evaporated
  8. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f7c643c346a54138afb7df751bd60203
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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