Aluminium lithium hydride → HCID 54449286, compound

HRID 650916Notes

Reaction equation

HRID 650916 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 Step A of Example 30 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-99b8847616cb42f8814df251453843e0
Source dataset
uspto-grants-2001_08
Patent number
US06277843B1

Reaction notes

Loading…