Aluminium lithium hydride → HCID 22499230, compound

HRID 244783Notes

Reaction equation

HRID 244783 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[C:16]([CH3:17])=[C:15]([CH3:18])[C:14]([CH3:19])=[C:13]2[C:9]=1[CH2:10][CH:11]([NH:20][C:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:12]2>O1CCCC1>[CH2:21]([NH:20][CH:11]1[CH2:12][C:13]2[C:9](=[C:8]([CH3:7])[C:16]([CH3:17])=[C:15]([CH3:18])[C:14]=2[CH3:19])[CH2:10]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 22499208HCID 22499208, compound

Product 1

HCID 22499230HCID 22499230, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
50 °C

Procedure

1M Lithium aluminium hydride (2.4 ml) in tetrahydrofuran is added dropwise to a solution of N-(4,5,6,7-tetramethyl-indan-2-yl)-benzamide (352 mg) in anhydrous THF (10 ml) under nitrogen at room temperature. The reaction mixture is allowed to stir at 50° C. for 20 hours. After 4 hours more 1M Lithium aluminium hydride (1.2 ml, 1.20 mmole) in THF is added. On cooling the reaction mixture is quenched with ice water. The aqueous phase is washed with diethyl ether (×3) and the organic layers combined, treated with magnesium sulphate, filtered and the solvent removed in vacuo.

Workup

  1. temperatureOn cooling the reaction mixture
  2. customis quenched with ice water
  3. washThe aqueous phase is washed with diethyl ether (×3)
  4. additiontreated with magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9155282cf3744b3fa6c3f39402cd0958
Source dataset
uspto-grants-2014_02
Patent number
US08658673B2

Reaction notes

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