Aluminium lithium hydride → HCID 118307113, compound

HRID 921239Notes

Reaction equation

HRID 921239 reaction equation
[CH2:1]([C:4]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:5]=1[C:6](OC)=[O:7])[CH:2]=[CH2:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([C:4]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:5]=1[CH2:6][OH:7])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 118307106HCID 118307106, compound

Product 1

HCID 118307113HCID 118307113, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 2-allyl-4-fluorobenzoate (400 mg, 2.060 mmol) in THF (5 mL) was added LAH (4.12 mL, 4.12 mmol) and the reaction was stirred at rt for 1 h. It was then added NH4Cl and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to isolate (2-allyl-4-fluorophenyl)methanol (300 mg, 1.805 mmol, 88% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.37 (dd, J=8.9, 6.0 Hz, 1H), 7.06-6.84 (m, 2H), 6.08-5.88 (m, 1H), 5.24-5.03 (m, 2H), 4.76-4.68 (m, 2H), 3.58-3.39 (m, 2H).

Workup

  1. extractionadded NH4Cl and extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto obtain an oil, which
  6. customwas then purified by biotage
  7. washeluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-34e2b70e3021478580fdfef01980f7d2
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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