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

HRID 921132Notes

Reaction equation

HRID 921132 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6](OC(CC=C)C)=[O:7])=[C:4]([O:16][C@H:17]([CH2:19][CH:20]=[CH2:21])[CH3:18])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][OH:7])=[C:4]([O:16][C@H:17]([CH2:19][CH:20]=[CH2:21])[CH3:18])[CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 118307121pent-4-en-2-yl 4-chloro-2-((S)-pent-4-en-2-yloxy)benzoate

Product 1

HCID 118307061(S)-(4-chloro-2-(pent-4-en-2-yloxy)phenyl)methanolYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of pent-4-en-2-yl 4-chloro-2-((S)-pent-4-en-2-yloxy)benzoate (1.36 g, 4.40 mmol) in THF (15 ml) that was cooled to 0° C. was added dropwise over 30 min lithium aluminum hydride (2.64 ml, 5.28 mmol) and the resulting mixture was stirred at rt. After 3 h, the mixture was cooled to 0° C. and quenched by dropwise addition of brine. The mixture was diluted with EtOAc and the organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The oil was purified by flash chromatography (Biotage; 0%-50% EtOAc/hexane; 10 CV) to give (S)-(4-chloro-2-(pent-4-en-2-yloxy)phenyl)methanol (0.9554 g, 4.21 mmol, 96% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.21 (d, J=7.8 Hz, 1H), 6.98-6.88 (m, 1H), 6.88 (d, J=1.7 Hz, 1H), 5.86 (ddt, J=17.1, 10.1, 7.1 Hz, 1H), 5.25-5.06 (m, 2H), 4.75-4.62 (m, 1H), 4.62-4.43 (m, 2H), 2.61-2.40 (m, 2H), 2.34 (t, J=6.5 Hz, 1H), 1.38 (d, J=6.1 Hz, 3H).

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. customquenched by dropwise addition of brine
  3. additionThe mixture was diluted with EtOAc
  4. washthe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe oil was purified by flash chromatography (Biotage; 0%-50% EtOAc/hexane; 10 CV)

Sources & evidence

ORD record
ord-4d2b8465334845af8cade2ce1ece2a9a
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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