Aluminium lithium hydride → HCID 86602918, compound

HRID 901770Notes

Reaction equation

HRID 901770 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:17]([O:27][C@@H:28]2[O:57][C@H:56]([CH:58](S(C3C(C)=CC=CC=3)(=O)=O)O)[C@@H:47]([O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C@H:38]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C@H:29]2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:16]([CH2:70][O:71][CH2:72][C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)[O:15][CH:10]1[O:11][CH2:12][CH:13]=[CH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C.[OH-].[Na+].O>[CH2:1]([O:8][C@@H:9]1[C@@H:18]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:17]([O:27][C@@H:28]2[O:57][C@H:56]([CH3:58])[C@@H:47]([O:48][CH2:49][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[C@H:38]([O:39][CH2:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C@H:29]2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:16]([CH2:70][O:71][CH2:72][C:73]2[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=2)[O:15][CH:10]1[O:11][CH2:12][CH:13]=[CH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86602916HCID 86602916, compound

Product 1

HCID 86602918HCID 86602918, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

The compound (32.6 g, 30.3 mol) synthesized in Example 2 (2d) was dissolved in diethyl ether (600 mL) and lithium aluminium hydride (1.72 g, 45.4 mol) was added thereto, followed by heating of the mixture under reflux for 1 hour. After the reaction mixture was diluted with diethyl ether (200 mL), 1N aqueous NaOH solution (2.0 mL) and water (2.0 mL) were added thereto, followed by stirring of the mixture for 30 minutes. After celite filtration, the solvent was distilled off under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:ethyl acetate, 7:1-6:1, V/V) to obtain the desired title compound (15.0 g, yield 55%) as a colorless solid.

Workup

  1. temperatureby heating of the mixture
  2. temperatureunder reflux for 1 hour
  3. additionwere added
  4. filtrationAfter celite filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-b8399979cea64831913a29c13d8da61b
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

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