Aluminium lithium hydride → HCID 18388551, compound

HRID 2297313Notes

Reaction equation

HRID 2297313 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)C>C1COCC1>[CH2:26]([O:25][C:22]1[CH:23]=[CH:24][C:19]([C:16]2[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][CH2:10][OH:9])=[CH:14][CH:15]=2)=[CH:20][CH:21]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54286881HCID 54286881, compound

Product 1

HCID 18388551HCID 18388551, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) stirred suspension of LiAlH4 (0.47 g, 12.4 mmol) in THF (20 ml) was added a solution of 3-(4′-heptyloxybiphenyl-4-yl)propionic acid ethyl ester (crude, 2.74 g) in THF (30 ml). After being stirred for 30 min. at room temperature, the mixture was quenched with H2O at 0° C. The mixture was filtered through a pad of Celite and washed with CH2Cl2. The filtrate and washings were combined and concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc/hexane, 2:3) to give 3-(4′-heptyloxy-biphenyl-4-yl)propan-1-ol (2.27 g, 96% for 2 steps) as a white amorphous powder.

Workup

  1. stirringAfter being stirred for 30 min. at room temperature
  2. customthe mixture was quenched with H2O at 0° C
  3. filtrationThe mixture was filtered through a pad of Celite
  4. washwashed with CH2Cl2
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (EtOAc/hexane, 2:3)

Sources & evidence

ORD record
ord-64332abb1ecb4725b172fe7e4e18155b
Source dataset
uspto-grants-2002_12
Patent number
US06489440B1

Reaction notes

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