Aluminium lithium hydride → HCID 86751499, compound

HRID 2292710Notes

Reaction equation

HRID 2292710 reaction equation
[F:1][C:2]1[C:7]2[C:8](=[O:32])[C:9](=[CH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:18]3[O:19][CH2:20][C:21]([CH3:24])([CH3:23])[N:22]=3)[O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[C:7]2[C:8]([OH:32])=[C:9]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:18]3[O:19][CH2:20][C:21]([CH3:23])([CH3:24])[N:22]=3)[O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86751500HCID 86751500, compound

Product 1

HCID 86751499HCID 86751499, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the compound from step A in THF (0.1M) at 0° C. was added LiAlH4 (1M in ether, 2.2 eq) dropwise over 10 minutes. The mixture was warmed to room temperature and stirred for 12 hours. The mixture was cooled to 0° C., quenched with Rochelles salt, and filtered through diatomaceous earth. The aqueous layer was extracted twice with ethylacetate, and the combined organic layers were washed with brine and dried over MgSO4. Filtration an solvent removal afforded a yellow oil. Chromatography over silica gel (ethylacetate:hexane) afforded a 60% yield of a white solid. M.P. 65°-70° C. (decomposed). Anal. calcd. for C27H26 NO3F: C, 75.15; H, 6.07; N, 3.25. Found: C, 74.75, H, 6.02, N, 3.09. 1H-NMR (300 MHz, CDCl3) :7.70 (1H, dd), 7.02-7.37 (8H, m), 6.96 (1H, dd), 7.91 (1H, d), 4.51 (1H, d), 4.23 (1H, dd), 4.39 (1H, dd) 3.87 (2H, dd), 2.74 (1H, dd), 2.55 (1H, dd), 2.18-2.28 (1H, m) 1.31 (6 H, d).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customquenched with Rochelles salt
  3. filtrationfiltered through diatomaceous earth
  4. extractionThe aqueous layer was extracted twice with ethylacetate
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationFiltration
  8. customan solvent removal
  9. customafforded a yellow oil

Sources & evidence

ORD record
ord-5f104390a5f943748909f60ea2d8b808
Source dataset
uspto-grants-1997_11
Patent number
US05684046

Reaction notes

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