Aluminium lithium hydride → HCID 67975401, compound

HRID 523469Notes

Reaction equation

HRID 523469 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[CH:15]=[C:14]1[C:22](OCC)=[O:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[CH:15]=[C:14]1[CH2:22][OH:23])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86698870HCID 86698870, compound

Product 1

HCID 67975401HCID 67975401, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 8-a (1.14 g, 3.14 mmol) in dry THF (100 mL) was added drop wise LAH (CAS 16853-85-3) (a 2M solution in THF, 1.89 mL, 3.77 mmol) at room temperature. The resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was quenched by addition of ethyl acetate and methanol. Then it was poured into an ice water solution. The resulting mixture was filtered on celite and the two layers were separated. The aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine (100 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The product was purified by flash column chromatography, eluting with heptane/ethyl acetate. After evaporation compound 8-b was obtained as a colorless oil (980 mg, 93%).

Workup

  1. customThe reaction mixture was quenched by addition of ethyl acetate and methanol
  2. additionThen it was poured into an ice water solution
  3. filtrationThe resulting mixture was filtered on celite
  4. customthe two layers were separated
  5. extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
  6. washThe combined organic extracts were washed with brine (100 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe product was purified by flash column chromatography
  11. washeluting with heptane/ethyl acetate
  12. customAfter evaporation compound 8-b

Sources & evidence

ORD record
ord-876ca170f35e4285955a7abce4c0a657
Source dataset
uspto-grants-2016_05
Patent number
US09339494B2

Reaction notes

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