Aluminium lithium hydride → HCID 22005208, compound

HRID 324833Notes

Reaction equation

HRID 324833 reaction equation
[CH:1]([C:4]1[C:9]([CH2:10][CH:11]=[O:12])=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:7]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:6]([CH:25]([CH3:27])[CH3:26])[N:5]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]([C:4]1[C:9]([CH2:10][CH2:11][OH:12])=[C:8]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[C:7]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:6]([CH:25]([CH3:26])[CH3:27])[N:5]=1)([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22005375HCID 22005375, compound

Product 1

HCID 22005208HCID 22005208, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the intermediate obtained in Step A (20 mg, 0.054 mmol) in dry THF (10 mL) was added dropwise LAH (2 eq., 1M, 0.11 mL) under argon and the mixture was stirred at reflux for 1 h. The reaction was quenched with water (3.9 μL), 20% NaOH (3.9 μL), and water (7.8 μL) again. Concentration afforded a white solid. The product was subjected to a pad of silica gel (CH2Cl2) to afford the title compound as a white solid (14 mg, 0.038mmol, 70%). 1H NMR (300 MHz, CDCl3): δ 7.39 (m, 2 H), 7.12 (m, 2 H), 3.52 (t, J=5.5 Hz, 2 H), 3.23 (m, 2 H), 2.60 (t, J=2.9 Hz, 2 H), 2.20 (t, J=3.7 Hz, 2 H), 1.30 (m, 14 H), 1.11 (m, 4 H), 0.771 (t, J=6.3 Hz, 3 H). FAB-MS: calcd for (C24H34FNO) 371, found 372 (M+H). Anal. Calcd for C24H34FNO: C, 77.59; H, 9.22; N, 3.77. Found: C, 77.57; H, 9.44; N, 3.05. mp 81-83° C. Rf=0.6 (10% ether/hexane).

Workup

  1. temperatureat reflux for 1 h
  2. customThe reaction was quenched with water (3.9 μL), 20% NaOH (3.9 μL), and water (7.8 μL) again
  3. concentrationConcentration
  4. customafforded a white solid

Sources & evidence

ORD record
ord-ade55173f3e344d3a9bc9055588fd01d
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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