Aluminium lithium hydride → HCID 69707851, compound

HRID 392913Notes

Reaction equation

HRID 392913 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:14][C:15](=O)[C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)C1C=CC=CC=1>>[CH2:24]([O:23][C:17]1[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=1[CH2:15][OH:14])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53694565HCID 53694565, compound

Product 1

HCID 69707851HCID 69707851, compoundYield 82%

Procedure

LAH (226 mg, 5.95 mmol) was added to a solution of 2-benzyloxy-5-fluoro-benzoic acid benzyl ester (2 g, 5.95 mmol) at 0° C. The reaction was warmed to room temperature and after 1 hour, the reaction was quenched by the sequential addition of water (226 μL), 15% NaOH (226 μL), and water (760 μL), the mixture was diluted with ethyl acetate and dried with MgSO4, filtered and concentrated. The residue was purified by flash chromatography (10% ethyl acetate/hexanes) to afford 1.13 g (82%) of the title compound as a colorless solid. MS 250 (M+NH4)+. 1H NMR (400 MHz, CDCl3) δ 7.4 (m, 5H); 7.05 (dd, 1H, J=9.1, 4.3 Hz); 6.92 (m, 2H); 5.08 (s, 2H); 4.65 (s, 2H); 2.2 (bs, 1H).

Workup

  1. customthe reaction was quenched by the sequential addition of water (226 μL), 15% NaOH (226 μL), and water (760 μL)
  2. additionthe mixture was diluted with ethyl acetate
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4ddc89971db146b1aa7cb5b5fc72cd7d
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Reaction notes

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