Aluminium lithium hydride → HCID 11426012, compound

HRID 552925Notes

Reaction equation

HRID 552925 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][N:15]([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57474450HCID 57474450, compound

Product 1

HCID 11426012HCID 11426012, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To an argon purged 250 mL round bottom flask fitted with condenser and magnetic stirbar containing 53 (1.283 g, 4.35 mmol) was added lithium aluminum hydride (412 mg, 10.86 mmol). Anhydrous tetrahydrofuran (15 mL) was added resulting in gas formation. The flask was placed in an oil bath and heated to 65° C. and stirred for 16 hours under argon. The reaction was cooled to room temperature and quenched with water (1.1 mL), 3N sodium hydroxide (1.7 mL) and water (3.3 mL) sequentially. The mixture was filtered to remove the white solid and the pale yellow filtrate concentrated to afford a pale yellow oil. Drying under high vacuum afforded a pale yellow solid, compound 54. Yield: 1.193 g of pale yellow solid (97.5%). 1H NMR (DMSO) δ 7.65-7.64 (d, 1H, J=1.5), 7.30-7.27 (d, 1H, J=8.7 Hz), 7.167 (s, 1 H), 7.14-7.09 (q, 1H, J=6.9, 8.4 Hz), 2.67-2.62 (t, J=7.5, 2H), 2.25-2.20 (t, J=7.5 Hz, 2H), 2.12 (s, 8 H).

Workup

  1. customTo an argon purged 250 mL round bottom flask
  2. customfitted with condenser
  3. customresulting in gas formation
  4. customThe flask was placed in an oil bath
  5. temperatureThe reaction was cooled to room temperature
  6. customquenched with water (1.1 mL), 3N sodium hydroxide (1.7 mL) and water (3.3 mL) sequentially
  7. filtrationThe mixture was filtered
  8. customto remove the white solid
  9. concentrationthe pale yellow filtrate concentrated
  10. customto afford a pale yellow oil
  11. customDrying under high vacuum

Sources & evidence

ORD record
ord-03a8e30e31ba426ca07ea9c0471511ec
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

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