Aluminium lithium hydride → HCID 66642809, compound

HRID 1170970Notes

Reaction equation

HRID 1170970 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([Cl:35])[C:17]=1[O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH:20]=1)[C:11](OC)=[O:12]>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([Cl:35])[C:17]=1[O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH:20]=1)[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66642868HCID 66642868, compound

Product 1

HCID 66642809HCID 66642809, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of LiAlH4 (0.26 g, 6.95 mmol) in THF (40 mL) at 0° C. was slowly added a solution of methyl 3,5-dichloro-4-[3′-(4-fluorobenzyl)-4′-methoxyphenoxy]benzoate (1.2 g, 2.76 mmol) in THF (10 mL). The reaction mixture was stirred at room temperature for 20 h and cooled to 0° C. The reaction mixture was quenched with 15% aqueous NaOH (1.5 mL), diluted with H2O (3.0 mL) and stirred for 1 h. The reaction mixture was filtered through a Celite plug and the filtrate was extracted with ethyl acetate (100 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (1:1) to afford 3,5-dichloro-4-[3′-(4-fluorobenzyl)-4′-methoxyphenoxy]benzyl alcohol as an oil (0.78 g, 70%): 1H NMR (300 MHz, CDCl3): δ 7.47 (s, 2 H), 7.16 (dd, J=6.0, 8.7 Hz, 2 H), 7.04 (t, J=8.7 Hz, 2 H), 6.84 (d, J=9.0 Hz, 1 H), 6.67 (d, J=3.0 Hz, 1 H), 6.45 (dd, J=5.4, 9.3 Hz, 1 H), 5.45 (t, J=5.7 Hz, 1 H), 4.48 (d, J=5.7 Hz, 2 H), 3.82 (s, 2 H), 3.69 (s, 3 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase ethyl acetate-hexanes (2:3); Rf=0.45.

Workup

  1. temperaturecooled to 0° C
  2. customThe reaction mixture was quenched with 15% aqueous NaOH (1.5 mL)
  3. additiondiluted with H2O (3.0 mL)
  4. stirringstirred for 1 h
  5. filtrationThe reaction mixture was filtered through a Celite plug
  6. extractionthe filtrate was extracted with ethyl acetate (100 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by column chromatography on silica gel
  11. washeluting with ethyl acetate-hexanes (1:1)

Sources & evidence

ORD record
ord-d4b97b4710084bc69089b376a1c82e6a
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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