Aluminium lithium hydride → HCID 67958076, compound

HRID 527593Notes

Reaction equation

HRID 527593 reaction equation
[CH3:1][C:2]12[CH2:12][CH:11]1[C:10]1[C:9]([O:13][CH2:14][O:15][CH3:16])=[CH:8][CH:7]=[CH:6][C:5]=1[O:4][C:3]2=[O:17].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C(OCC)(=O)C>[OH:17][CH2:3][C:2]1([CH3:1])[CH2:12][CH:11]1[C:10]1[C:9]([O:13][CH2:14][O:15][CH3:16])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:4]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67966894HCID 67966894, compound2×

Product 1

HCID 67958076HCID 67958076, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1a-methyl-7-{[(methyloxy)methyl]oxy}-1a,7b-dihydrocyclopropa[c]chromen-2(1H)-one (Intermediate 122, 360 mg) in dry tetrahydrofuran (15 ml) stirred under nitrogen at 0° C. was added a solution of lithium aluminium hydride (1.0M in THF, 1.537 ml, 1.537 mmol) and the reaction mixture was stirred at that temperature for 20 minutes. The reaction was then diluted with THF (20 ml) and quenched with the addition of Na2SO4.10H2O (10 eq) leaving the mixture under stirring for 30 minutes. The reaction was diluted with ethyl acetate, dried over Na2SO4, filtered and concentrated under vacuum. The residue obtained was purified by silica gel chromatography (Companion system, with a gradient from cyclohexane/ethyl acetate 5/1 to cyclohexane/ethyl acetate 1/1) to give the title compound as a white solid (307 mg).

Workup

  1. customleaving the mixture
  2. stirringunder stirring for 30 minutes
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue obtained
  7. customwas purified by silica gel chromatography (Companion system

Sources & evidence

ORD record
ord-7295792b2651406cb8185bd6a1572801
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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