Aluminium lithium hydride → (S)-(1-(pent-4-en-2-yloxy)naphthalen-2-yl)methanol

HRID 921219Notes

Reaction equation

HRID 921219 reaction equation
[CH3:1][C@H:2]([O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[C:17](OC)=[O:18])[CH2:3][CH:4]=[CH2:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C@H:2]([O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[CH2:17][OH:18])[CH2:3][CH:4]=[CH2:5]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 118307160(S)-methyl 1-(pent-4-en-2-yloxy)-2-naphthoate

Product 1

HCID 118307011(S)-(1-(pent-4-en-2-yloxy)naphthalen-2-yl)methanolYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (S)-methyl 1-(pent-4-en-2-yloxy)-2-naphthoate (300 mg, 1.110 mmol) in THF (10 mL) was added 1 N LAH (2.220 mL, 2.220 mmol) and the reaction was stirred at rt for 1 h. It was then quenched with 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 (S)-(1-(pent-4-en-2-yloxy)naphthalen-2-yl)methanol (200 mg, 0.825 mmol, 74.4% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 8.19-8.08 (m, 1H), 7.90-7.80 (m, 1H), 7.65 (d, J=8.3 Hz, 1H), 7.58-7.45 (m, 3H), 5.96 (ddt, J=17.1, 10.1, 7.2 Hz, 1H), 5.25-5.11 (m, 2H), 4.93 (qd, J=12.6, 5.9 Hz, 2H), 4.54-4.34 (m, 1H), 2.65 (qd, J=6.8, 5.5 Hz, 1H), 2.59-2.48 (m, 1H), 2.18 (t, J=6.0 Hz, 1H), 1.31 (d, J=6.4 Hz, 3H).

Workup

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

Sources & evidence

ORD record
ord-d6d133d3b3b14ca0bba53e3bdb1bb343
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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