Lithium aluminum hydride → HCID 20031070, compound

HRID 232146Notes

Reaction equation

HRID 232146 reaction equation
[Li+].[AlH4-].[F:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]3[CH2:15][CH2:16][CH2:17][C:13]=3[C:12]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24])=[N:11]2)=[CH:6][CH:5]=1>C1COCC1>[F:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14]3[CH2:15][CH2:16][CH2:17][C:13]=3[C:12]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])=[N:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 14576185HCID 14576185, compound

Product 1

HCID 20031070HCID 20031070, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Lithium tetrahydridoaluminate (0.345 g, 9.1 mmol) in THF (75 ml) was treated with the compound of Example 31 (1.0 g, 3.1 mmol) and the mixture was heated at 60° C. for 2 hours. Excess reagent was quenched, the mixture filtered and the combined filtrate and ethyl acetate washes were evaporated to a colorless oil (0.76 g). Polar impurities were removed on silica gel (40 g) with 1:1 ethyl acetate-Skelly B eluent to provide title compound (0.42 g) as an oil.

Workup

  1. customExcess reagent was quenched
  2. filtrationthe mixture filtered
  3. customthe combined filtrate and ethyl acetate washes were evaporated to a colorless oil (0.76 g)
  4. customPolar impurities were removed on silica gel (40 g) with 1:1 ethyl acetate-Skelly B eluent

Sources & evidence

ORD record
ord-5dbc443e95534e3c9b94a293ff1a7720
Source dataset
uspto-grants-1989_07
Patent number
US04851425

Reaction notes

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