HCID 10890148, compound → HCID 69869174, compound

HRID 1883229Notes

Reaction equation

HRID 1883229 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH:14]([CH3:16])[CH3:15])[CH:13]=1)[O:10][C:9](=[O:17])[CH:8]=[C:7]2[CH3:18])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[OH:17][CH2:9][CH:8]=[C:7]([C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[C:11]=1[OH:10])[CH3:18]

Participants

4

Reactant 2

HCID 10890148HCID 10890148, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 69869174HCID 69869174, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6,8-diisopropyl-4-methylchromen-2-one Intermediate 11, 2.6 g, 10.7 mmol) in Et2O (100 mL) at 0° C. was added LiAlH4 portionwise (405 mg, 10.7 mmol). The reaction was stirred at 0° C. for 1 h, quenched by careful addition of ice, and acidified with 1M HCl. The mixture was then extracted with EtOAc. The organic layer was separated, washed successively with H2O, brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (20% EtOAc-hexanes) to yield the title compound as a nearly colorless syrup (1.82 g, 70%).

Workup

  1. customquenched by careful addition of ice
  2. extractionThe mixture was then extracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed successively with H2O, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel (20% EtOAc-hexanes)

Sources & evidence

ORD record
ord-a73bc2aeb9ed48f0b87e4cc5c82b1b22
Source dataset
uspto-grants-2004_07
Patent number
US06759546B1

Reaction notes

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