Ethyl Acetate → HCID 57568187, compound

HRID 549654Notes

Reaction equation

HRID 549654 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([SiH:16]([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])=[CH:12][CH:11]=1.C(OCC)(=O)C>C1COCC1.ClCCl>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([SiH:16]([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:18])[CH3:19])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 123864731HCID 123864731, compound

Product 1

HCID 57568187HCID 57568187, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (1.2 g, 32 mmol) was dissolved in anhydrous THF (80 mL), and to this was slowly added dropwise the anhydrous THF solution (80 mL) 4-diisopropylsilanylbenzoic acid methyl ester (2) (8 g, 32 mmol). The resulting mixture was then stirred for 10 min and ethyl acetate (20 mL) was added slowly to it. The reaction mixture was diluted with dichloromethane (500 mL), and then extracted three times with 0.2 N hydrochloric acid aqueous solution (400 mL). An organic layer was collected and dehydrated with anhydrous sodium sulfate and filtered so that the resulting solvent was distilled out under a reduced pressure to give a desired product (7.2 g, quant). Its NMR data are as follows:

Workup

  1. extractionextracted three times with 0.2 N hydrochloric acid aqueous solution (400 mL)
  2. customAn organic layer was collected
  3. filtrationfiltered so that the resulting solvent
  4. distillationwas distilled out under a reduced pressure

Sources & evidence

ORD record
ord-b242be3745e04aedbaa0e9c9bc7da696
Source dataset
uspto-grants-2011_05
Patent number
US07943758B2

Reaction notes

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