Aluminium lithium hydride → HCID 11244656, compound

HRID 1716135Notes

Reaction equation

HRID 1716135 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[C:21]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:21]1(=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH2:4][OH:3])=[CH:8][CH:9]=2)[C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86613511HCID 86613511, compound

Product 1

HCID 11244656HCID 11244656, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (5° C.) solution of ethyl({4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}oxy)acetate (190) (0.200 g, 0.53 mmol) in THF (10 mL) was added 1 M solution of LiAlH4 (1.3 mL, 2.5 mmol). The reaction mixture was stirred at that temperature for 0.5 h. Reaction mixture was quenched with EtOAc (5 mL) and stirred for an additional 10 min before pouring into 20% aqueous HCl (50 ml). The reaction mixture was extracted with EtOAc (3×50 mL) and the combined organics washed with brine (1×25 ml), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel using hexanes and EtOAc (4:1 to 3:2) as an eluent to afford 155 mg (86%) of compound 224 as a white solid. 1H NMR (300 MHz, CD3OD): δ 7.04 (d, J=8.7 Hz, 2H), 6.94 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 6.70 (d, J=8.4 Hz, 2H), 4.03 (t, J=5.1 Hz, 2H), 3.86 (t, J=5.1 Hz, 2H), 2.32 (d, J=4.5 Hz, 4H), 1.60 (br s, 8H). LCMS (ESI): m/z 337 (M−H)−.

Workup

  1. customReaction mixture
  2. customwas quenched with EtOAc (5 mL)
  3. stirringstirred for an additional 10 min
  4. additionbefore pouring into 20% aqueous HCl (50 ml)
  5. extractionThe reaction mixture was extracted with EtOAc (3×50 mL)
  6. washthe combined organics washed with brine (1×25 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-71a8704c8fc54b98bbc04388bc723be1
Source dataset
uspto-grants-2010_09
Patent number
US07799828B2

Reaction notes

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