Aluminium lithium hydride → HCID 59160998, compound

HRID 1873558Notes

Reaction equation

HRID 1873558 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][O:21][CH:22]1[CH2:27][CH2:26][CH:25]([C:28](OC)=[O:29])[CH2:24][CH2:23]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[Si:1]([O:18][CH2:19][CH2:20][O:21][CH:22]1[CH2:27][CH2:26][CH:25]([CH2:28][OH:29])[CH2:24][CH2:23]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 59161057HCID 59161057, compound

Product 1

HCID 59160998HCID 59160998, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1.90 g (3.75 mmol, 87% pure) of the compound from Example 3A are dissolved in 15 ml of diethyl ether and added dropwise to a suspension of 170.9 mg (4.50 mmol) of lithium aluminum hydride in 15 ml of diethyl ether. The mixture is then stirred at RT for 20 h. A further 136.7 mg (3.60 mmol) of lithium aluminum hydride are then added, and the mixture is stirred at RT for another 20 h. The mixture is then triturated with 257 μl of water and 257 μl of 15% strength aqueous potassium hydroxide solution. A further 10 ml of water are added, and the phases are separated. The organic phase is dried over magnesium sulfate. The solvent is removed on a rotary evaporator and the residue is purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 50:1→10:1).

Workup

  1. stirringthe mixture is stirred at RT for another 20 h
  2. customThe mixture is then triturated with 257 μl of water and 257 μl of 15% strength aqueous potassium hydroxide solution
  3. additionA further 10 ml of water are added
  4. customthe phases are separated
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customThe solvent is removed on a rotary evaporator
  7. customthe residue is purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 50:1→10:1)

Sources & evidence

ORD record
ord-89d71880be204f2dbec07df95a3f56ba
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

Loading…