Aluminium lithium hydride → HCID 18993688, compound

HRID 375774Notes

Reaction equation

HRID 375774 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[Br:16])[CH2:9][CH2:8][C:7]1=[O:17].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[Br:16][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH:6]([CH2:5][CH2:4][CH2:3][OH:2])[CH:7]([OH:17])[CH2:8][CH2:9]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54255154HCID 54255154, compound

Product 1

HCID 18993688HCID 18993688, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 8-bromo-1,2,3,4-tetrahydro-2-oxo-naphthalenepropionic acid methyl ester (B-2, 31.12 g, 0.100 mol) in diethylether (100 mls) was added to an ice-cooled suspension of lithium aluminum hydride (8.0 g, 0.21 mol) with stirring. The cold bath was removed, and the mixture was stirred at room temperature for 2 hours. The mixture was cooled in ice, and water (8.0 mls), 15% NaOH (8.0 mls), and water 24.0 mls) were added in succession. The mixture was stirred at room temperature for two hours and filtered. The precipitate was washed with tetrahydrofuran, and the combined flitrate was dried (MgSO4, and the solvent was removed under vacuum to leave the title compound as an oil (B-3, 29.2 g, 100%). NMR (CDCl3, TMS) δ1.35 (m, 1H), 1.7-2.1 (M,5H), 2.7-3.15 (m, 3H), 3.35-3.45 (m, 1H), 3.45-3.57 (m, 1H), 3.57-3.82 (m,2H), 4.0-4.15 (m,1H), 6.9-7.1 (m,2H), 7.38 (dd, 1H). IR (Major peaks) 3345, 3055, 1591, 1559, 1454, 1433, 1060, 767. Mass spec. m+at m/z 284, 285.

Workup

  1. temperaturecooled
  2. customThe cold bath was removed
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. temperatureThe mixture was cooled in ice
  5. additionwater (8.0 mls), 15% NaOH (8.0 mls), and water 24.0 mls) were added in succession
  6. stirringThe mixture was stirred at room temperature for two hours
  7. filtrationfiltered
  8. washThe precipitate was washed with tetrahydrofuran
  9. dry with materialthe combined flitrate was dried (MgSO4
  10. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-74d75342758445b4bdd2ccc1c5c7cc45
Source dataset
uspto-grants-1996_01
Patent number
US05486611

Reaction notes

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