Aluminium lithium hydride → HCID 58303884, compound

HRID 1404114Notes

Reaction equation

HRID 1404114 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]2[C:10]=1[C:11]([C:19](=O)[C:20](OC)=[O:21])=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]2[C:10]=1[C:11]([CH2:19][CH2:20][OH:21])=[CH:12][NH:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58303879HCID 58303879, compound

Product 1

HCID 58303884HCID 58303884, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A crude of 26-1 (2.32 mmol) and LiAlH4 (1.32 g, 34.8 mmol) in 100 mL dioxane was heated at reflux for 2 h. The reaction mixture was cooled to 0° C. and quenched by water, 15% NaOH and then water. The resulting suspension was stirred for 30 min, and then filtered. After dried over Na2SO4, the organic phase was concentrated to give a brown oil, which was purified by flash column chromatography, eluting with hexanes/EtOAc (8:1 to 1:1) to afford 26-2 as a white solid (259 mg, 39%). 1H NMR (CDCl3) (ppm): 7.98 (bs, 1H), 7.35-7.48 (m, 5H), 6.91 (d, J=2.5 Hz, 1H), 6.68 (dd, J1=1.9 Hz, J2=9.2 Hz, 1H), 6.39 (dd, J1=1.9 Hz, J2=11.5 Hz, 1H), 5.14 (s, 2H), 6.81 (q, J=6.3 Hz, 2H), 3.07 (t, J=6.3 Hz, 2H), 1.47 (t, J=6.0 Hz, 1H).

Workup

  1. temperatureat reflux for 2 h
  2. customquenched by water, 15% NaOH
  3. filtrationfiltered
  4. dry with materialAfter dried over Na2SO4
  5. concentrationthe organic phase was concentrated
  6. customto give a brown oil, which
  7. customwas purified by flash column chromatography
  8. washeluting with hexanes/EtOAc (8:1 to 1:1)

Sources & evidence

ORD record
ord-03751dbea61b43de834504ac86fc6a1f
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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