Lithium → HCID 10193121, compound

HRID 1835991Notes

Reaction equation

HRID 1835991 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[O:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([F:22])[CH:15]=3)=[CH:10][C:9]=2[CH:8]=[C:7]([O:23][CH3:24])[CH:6]=1)=O.[Li]>C1COCC1>[F:22][C:16]1[CH:15]=[C:14]([C:11]2[O:12][C:13]3[C:5]([CH2:3][OH:2])=[CH:6][C:7]([O:23][CH3:24])=[CH:8][C:9]=3[CH:10]=2)[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]

Participants

4

Reactant 2

HCID 3028194LithiumHCID 10286597HCID 10286597, compound

Product 1

HCID 10193121HCID 10193121, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Fluoro ester 40 (1.00 g, 3.63 mmole), was dissolved in 40 mL THF and stirred under nitrogen. To this solution was added lithium aluminumhydride (1M in THF, 3.81 mL, 3.81 mmole) dropwise over fifteen minutes. After stirring at rt for one half hour, the solvent was removed and the mixture was poured into 2N HCl and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 4:1) to afford 0.800 g (73%) of benzyl alcohol 41 as a tan solid: Mp=128-130° C.; 1H NMR (DMSO-d6) δ 7.78 (dd, 1 H, J=12.5 Hz, 2.0 Hz), 7.69 (dd, 1 H, J=8.7 Hz, 1.1 Hz), 7.29 (t, 2 H, J=8.1 Hz), 7.01 (d, 1 H, J=2.5 Hz), 6.90 (d, 1 H, J=2.5 Hz), 5.37 (br s, 1 H), 4.81 (d, 2 H, J=3.1 Hz), 3.90 (s, 3 H), 3.81 (s, 3 H); MS 303 (M+H)+

Workup

  1. stirringAfter stirring at rt for one half hour
  2. customthe solvent was removed
  3. additionthe mixture was poured into 2N HCl
  4. extractionextracted with ethyl acetate
  5. washThe combined organic phases were washed with saturated sodium bicarbonate, water, brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationThe organic phases were concentrated
  8. customchromatographed with silica gel (hexanes:ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-66177756205944438d2a643187a6e802
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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