Aluminium lithium hydride → HCID 57803535, compound

HRID 2103057Notes

Reaction equation

HRID 2103057 reaction equation
C([O:4][C:5]1[C:6]([CH2:22][CH3:23])=[C:7]2[C:15](=[CH:16][C:17]=1[CH:18]([CH3:20])[CH3:19])[O:14][C:10]1([CH2:13][CH2:12][CH2:11]1)[CH2:9][C:8]2=[O:21])(=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:22]([C:6]1[C:5]([OH:4])=[C:17]([CH:18]([CH3:20])[CH3:19])[CH:16]=[C:15]2[C:7]=1[CH:8]([OH:21])[CH2:9][C:10]1([O:14]2)[CH2:13][CH2:12][CH2:11]1)[CH3:23]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69053882HCID 69053882, compound

Product 1

HCID 57803535HCID 57803535, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-ethyl-7-isopropyl-4-oxospiro[chroman-2,1′-cyclobutane]-6-yl acetate (53 mg) in 5 mL of THF was added LiAlH4 (65 mg) in 3 portions at room temperature. The mixture was stirred for 2 h and quenched by pouring onto ice. The mixture was extracted with EtOAc (3×10 mL) and the organic extract was dried over Na2SO4 and concentrated. The crude product was purified by chromatography to afford 5-ethyl-7-isopropylspiro[chroman-2,1′-cyclobutane]-4,6-diol as an off-white solid (29 mg, 63%).

Workup

  1. customquenched
  2. additionby pouring onto ice
  3. extractionThe mixture was extracted with EtOAc (3×10 mL)
  4. extractionthe organic extract
  5. dry with materialwas dried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-760ddbe8224c43b49e8f560794d561cc
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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