HCID 19385657, compound → HCID 19385618, compound

HRID 2399493Notes

Reaction equation

HRID 2399493 reaction equation
[Si:1]([O:8][C:9]1[C:18]([Cl:19])=[CH:17][C:12]([C:13](OC)=[O:14])=[CH:11][C:10]=1[Cl:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Si:1]([O:8][C:9]1[C:10]([Cl:20])=[CH:11][C:12]([CH2:13][OH:14])=[CH:17][C:18]=1[Cl:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 19385657HCID 19385657, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19385618HCID 19385618, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and cooled (0° C.) solution of 7.70 g (23.0 mmol) of the product of Step A dissolved in 50 mL of anhydrous THF was added 23.0 mL (23.0 mmol) of a 1M solution of lithium aluminum hydride in THF. After the addition was complete the reaction mixture was allowed to warm to room temperature and stirred 3.5 hours. The stirred reaction was then quenched by dropwise addition of 0.88 mL water, then 0.88 mL of 15% NaOH, and finally 2.62 mL water. The reaction mixture was then filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with 1N HCl, saturated NaHCO3, dried (MgSO4), and evaporated in vacuo to afford 1.83 g (26%) of the title compound.

Workup

  1. additionAfter the addition
  2. stirringstirred 3.5 hours
  3. customThe stirred reaction
  4. customwas then quenched by dropwise addition of 0.88 mL water
  5. filtrationThe reaction mixture was then filtered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. washwashed with 1N HCl, saturated NaHCO3
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-7cf8b39358bf47d28551f308789bd26b
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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