Aluminium lithium hydride → HCID 22345511, compound

HRID 584158Notes

Reaction equation

HRID 584158 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:35]=[CH:34][C:25]([O:26][C:27]([CH3:33])([CH3:32])[C:28](OC)=[O:29])=[CH:24][CH: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][CH2:21][C:22]1[CH:35]=[CH:34][C:25]([O:26][C:27]([CH3:33])([CH3:32])[CH2:28][OH:29])=[CH:24][CH:23]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22345523HCID 22345523, compound

Product 1

HCID 22345511HCID 22345511, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of methyl 2-[4-[3-(tert-butyldiphenylsilyloxy)propyl]phenoxy]-2-methylpropionate (5.88 g, 11.98 mmol) in diethyl ether (100 ml) was treated at 22° C. with 23 ml (23 mmol) of a 1M solution of lithium aluminum hydride in ether. The resulting mixture was then heated under reflux for 1 hour. The cooled mixture was quenched by addition of ethyl acetate, water (5 ml) and 1N sodium hydroxide (5 ml). The solid formed was filtered and the filtrate was evaporated and purified on silica gel. Elution with a mixture of toluene and ethyl acetate (9:1) gave 5.14 g (93%) of the title material as an oil.

Workup

  1. temperatureThe resulting mixture was then heated
  2. temperatureunder reflux for 1 hour
  3. customThe cooled mixture was quenched by addition of ethyl acetate, water (5 ml) and 1N sodium hydroxide (5 ml)
  4. customThe solid formed
  5. filtrationwas filtered
  6. customthe filtrate was evaporated
  7. custompurified on silica gel
  8. washElution
  9. additionwith a mixture of toluene and ethyl acetate (9:1)

Sources & evidence

ORD record
ord-9c1d642aa96f4ae3a0553f39678310df
Source dataset
uspto-grants-2005_08
Patent number
US06924391B2

Reaction notes

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