Aluminium lithium hydride → HCID 66994358, compound

HRID 251621Notes

Reaction equation

HRID 251621 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]1[C:16]([CH3:17])=[CH:15][C:14]([C:18]2[C:23]([CH2:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:26][CH3:27])=[N:13][C:12]=1[CH3:28])C>C1COCC1>[CH2:24]([C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:26][CH3:27])[C:18]=1[C:14]1[N:13]=[C:12]([CH3:28])[C:11]([CH2:10][OH:9])=[C:16]([CH3:17])[CH:15]=1)[CH3:25]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66993644HCID 66993644, compound

Product 1

HCID 66994358HCID 66994358, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (2.4 mL of 1M solution in THF, 2.44 mmol) is added to a solution of 6-(2,6-diethyl-phenyl)-2,4-dimethyl-nicotinic acid ethyl ester (380 mg, 1.22 mmol) in THF (10 mL) at 0° C. The mixture is stirred for 1 hour at ambient temperature. After quenching with water, the mixture is extracted with EtOAc. The combined extracts are washed with saturated brine, dried (NaaSO4), and concentrated to give the crude alcohol as a colorless oil which is used in the next step without further purification. NMR (CDCl3) 7.26 (t, 1H), 7.13 (d, 2H), 6.93 (s, 1H), 4.82 (s, 2H), 2.68 (s, 3H), 2.46 (s, 3H), 2.37-2.28 (m, 4H), 1.05 (t, 6H).

Workup

  1. customAfter quenching with water
  2. extractionthe mixture is extracted with EtOAc
  3. washThe combined extracts are washed with saturated brine
  4. customdried (NaaSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8fee652c0a044ba2bd2ed21ce9c6bb57
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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