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

HRID 921120Notes

Reaction equation

HRID 921120 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C@H: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>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C@H: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 118307101(S)-methyl 5-methyl-2-(pent-4-en-2-yloxy)benzoate

Product 1

HCID 118307102(S)-(5-methyl-2-(pent-4-en-2-yloxy)phenyl)methanolYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 5-methyl-2-(pent-4-en-2-yloxy)benzoate (1.2664 g, 5.41 mmol) in THF (15 ml) cooled to 0° C. was added dropwise lithium aluminum hydride (3.25 ml, 6.49 mmol). The mixture was stirred at rt for 2 h then cooled to 0° C. and quenched by the dropwise addition of brine. The mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated to give (S)-(5-methyl-2-(pent-4-en-2-yloxy)phenyl)methanol (0.8702 g, 4.22 mmol, 78% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.14-7.01 (m, 2H), 6.80 (d, J=8.1 Hz, 1H), 6.01-5.74 (m, 1H), 5.24-5.04 (m, 2H), 4.76-4.64 (m, 1H), 4.64-4.56 (m, 1H), 4.51 (sxt, J=6.0 Hz, 1H), 2.63-2.48 (m, 2H), 2.48-2.41 (m, 1H), 2.30 (s, 3H), 1.37 (d, J=6.1 Hz, 3H).

Workup

  1. temperaturethen cooled to 0° C.
  2. customquenched by the dropwise addition of brine
  3. customThe mixture was partitioned between EtOAc and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8dd5da171a5c48de98d3ce5b4feabcca
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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