Aluminium lithium hydride → HCID 66994358, compound

HRID 1392653Notes

Reaction equation

HRID 1392653 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-34ef9c4e6fa940d0b00a2289e62e2efc
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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