Aluminium lithium hydride → HCID 59415730, compound

HRID 473070Notes

Reaction equation

HRID 473070 reaction equation
C([O:3][C:4]([C:6]1([CH3:20])[CH2:14][C:13]2[C:8](=[C:9]([CH3:18])[C:10]([CH:16]=[CH2:17])=[C:11]([CH3:15])[CH:12]=2)[C:7]1=[O:19])=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:3][CH2:4][C:6]1([CH3:20])[CH2:14][C:13]2[C:8](=[C:9]([CH3:18])[C:10]([CH:16]=[CH2:17])=[C:11]([CH3:15])[CH:12]=2)[CH:7]1[OH:19]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 594157222,5,7-Trimethyl-1-oxo-6-vinyl-indan-2-carboxylic acid ethyl ester

Product 1

HCID 59415730HCID 59415730, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To the stirred solution of compound 6 (1.3 g, 4.77 mmol) in dry THF (10 mL) was added LAH (0.212 g, 5.73 mmol) at −78° C. under argon atmosphere and stirred the reaction mixture for 3 h then the reaction mixture was warmed to 0° C. and quenched with ethyl acetate (30 mL) at 0° C. After the reaction mixture was back to room temperature, extracted with 2M potassium sodium tartrate solution, washed with, brine (20 mL) dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography (SiO2, 15 to 20% EtOAc in petroleum ether eluant) gave pure compound 7 (0.88 g, 80%) as gummy syrup.

Workup

  1. customquenched with ethyl acetate (30 mL) at 0° C
  2. customwas back to room temperature
  3. extractionextracted with 2M potassium sodium tartrate solution
  4. washwashed with, brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (SiO2, 15 to 20% EtOAc in petroleum ether eluant)

Sources & evidence

ORD record
ord-f25484ea25174d23a8fbeba639f60913
Source dataset
uspto-grants-2014_01
Patent number
US08633252B2

Reaction notes

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