Aluminium lithium hydride → HCID 54449286, compound

HRID 1533453Notes

Reaction equation

HRID 1533453 reaction equation
[OH:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]([CH2:15][C:16](OC)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC>[OH:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]([CH2:15][CH2:16][OH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21706145HCID 21706145, compound

Product 1

HCID 54449286HCID 54449286, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 277.5 mg (1.09 mmol) of the ester prepared in Example 14 in 5 mL of anhydrous THF at 0° C. was added dropwise 1.1 mL (1.1 mmol) of a 1M solution of lithium aluminum hydride in ether. The resulting mixture was stirred at 0° C. under nitrogen for 1.5 hours and then carefully quenched with Glaubers salt. The mixture was partitioned between EtOAc, ice, 2N HCl, and brine and the organic phase was separated, washed with brine, dried over Na2SO4, filtered, and evaporated. The residue was purified by PLC with CH2Cl2-EtOAc (10:1) to give 236.8 mg of the title compound.

Workup

  1. customcarefully quenched with Glaubers salt
  2. customThe mixture was partitioned between EtOAc, ice, 2N HCl, and brine
  3. customthe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by PLC with CH2Cl2-EtOAc (10:1)

Sources & evidence

ORD record
ord-5929fafff00e4275a329712d7a510bb0
Source dataset
uspto-grants-2001_03
Patent number
US06207823B1

Reaction notes

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