Aluminium lithium hydride → HCID 59644267, compound

HRID 2252093Notes

Reaction equation

HRID 2252093 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=[C:27]([CH3:35])[CH:26]=3)[CH:19]=2)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=[C:27]([CH3:35])[CH:26]=3)[CH:19]=2)[OH:17])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58958057HCID 58958057, compound

Product 1

HCID 59644267HCID 59644267, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 209 (0.15 g, 0.32 mmol) in THF (5.0 ml) was added LAH (1.0 M in THF, 0.66 ml, 0.66 mmol) at 0° C. The mixture was stirred at room temperature overnight before it was quenched with Na2SO4.10H2O (pellets) until no further bubbles was observed. The mixture was diluted with ethyl acetate and the solids filtered. The filterate was washed with water (50 ml), brine (50 ml), dried over MgSO4 and concentrated on a rotovap to give the desired alcohol as a yellow solid (0.04 g, 27%).

Workup

  1. customwas quenched with Na2SO4.10H2O (pellets) until no further bubbles
  2. additionThe mixture was diluted with ethyl acetate
  3. filtrationthe solids filtered
  4. washThe filterate was washed with water (50 ml), brine (50 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated on a rotovap

Sources & evidence

ORD record
ord-6bd62ef3ed5144c4a6eaf8a1b3e4c67d
Source dataset
uspto-grants-2008_01
Patent number
US07320989B2

Reaction notes

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