Aluminium lithium hydride → (5-Fluoro-2-(pent-4-en-2-yloxy)phenyl)methanol

HRID 921110Notes

Reaction equation

HRID 921110 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH:13]([CH2:15][CH:16]=[CH2:17])[CH3:14])=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH:13]([CH2:15][CH:16]=[CH2:17])[CH3:14])=[C:6]([CH2:7][OH:8])[CH:11]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 118307052Methyl 5-fluoro-2-(pent-4-en-2-yloxy)benzoate

Product 1

HCID 118307027(5-Fluoro-2-(pent-4-en-2-yloxy)phenyl)methanolYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 5-fluoro-2-(pent-4-en-2-yloxy)benzoate (1.00 g, 4.20 mmol) in THF (10 mL) cooled to 0° C. was added dropwise lithium aluminum hydride (5.04 ml, 5.04 mmol) over 30 min. The resulting mixture was stirred at rt for 2 h. The reaction was diluted with 2 mL THF and cooled to 0° C. and quenched by the dropwise addition of brine. The mixture was further diluted with 5 mL EtOAc and the organic phase was decanted off, dried (Na2SO4), filtered and concentrated to give (5-fluoro-2-(pent-4-en-2-yloxy)phenyl)methanol (0.80 g, 3.81 mmol, 91% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.04 (dd, J=8.7, 3.1 Hz, 1H), 6.93 (td, J=8.5, 3.1 Hz, 1H), 6.82 (dd, J=8.9, 4.3 Hz, 1H), 5.86 (ddt, J=17.1, 10.1, 7.1 Hz, 1H), 5.25-5.06 (m, 2H), 4.75-4.54 (m, 2H), 4.54-4.38 (m, 1H), 2.51 (dt, J=13.9, 6.7 Hz, 2H), 1.42-1.31 (m, 3H).

Workup

  1. temperaturecooled to 0° C.
  2. customquenched by the dropwise addition of brine
  3. additionThe mixture was further diluted with 5 mL EtOAc
  4. customthe organic phase was decanted off
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f054fb8ee167461d997490228f25cfcb
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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