Aluminium lithium hydride → HCID 69491132, compound

HRID 851971Notes

Reaction equation

HRID 851971 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[C:13]([F:26])[CH:12]=1)C>C1COCC1>[F:26][C:13]1[CH:12]=[C:11]([CH2:10][OH:9])[CH:16]=[CH:15][C:14]=1[O:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69489153HCID 69489153, compound

Product 1

HCID 69491132HCID 69491132, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To lithium aluminium hydride (0.03 g, 0.90 mmol) suspended in dry THF (1 ml) and cooled to 0° C. under an argon atmosphere was added a solution of 3-fluoro-4-(2-morpholin-4-yl-ethoxy)-benzoic acid ethyl ester (0.15 g, 0.5 mmol) in dry THF (1 ml). The cold bath was removed and the reaction mixture further stirred for 2 h at r.t. The reaction mixture was cooled (0° C.) and quenched with NaHCO3 (½ sat., 2 ml) and further stirred for 0.5 h at r.t., filtered and concentrated under reduced pressure. The filtrate was dissolved in ethyl acetate and washed with water (2×), brine, dried (MgSO4) filtered and concentrated under reduced pressure: 0.12 g (86%);

Workup

  1. customThe cold bath was removed
  2. temperatureThe reaction mixture was cooled (0° C.)
  3. customquenched with NaHCO3 (½ sat., 2 ml)
  4. stirringfurther stirred for 0.5 h at r.t.
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe filtrate was dissolved in ethyl acetate
  8. washwashed with water (2×), brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bea499c3b0d3452b81f0d5f31a2a6b3a
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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