Aluminium lithium hydride → HCID 54003381, compound

HRID 363047Notes

Reaction equation

HRID 363047 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=O)[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[C:11]([CH2:23][CH3:24])[CH:10]=2)=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:23]([C:11]1[CH:10]=[C:9]([CH2:8][NH:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:14]=[CH:13][C:12]=1[O:15][CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1)[CH3:24]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54465861HCID 54465861, compound

Product 1

HCID 54003381HCID 54003381, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 23-7 (290 mg, 0.86 mmol) in 5 mL of THF was added 1.7 mL (1.7 mmol) of LiAlH4 (1M in THF) and the resulting solution was heated at 50° C. for 2 h, cooled to 0° C. and quenched with 0.07 mL of water, 0.07 mL of 15% NaOH and 0.2 mL of water. The precipitate was filtered, concentrated and purified by column chromatography (94:6:0.6 CHCl3 /IPA/NH4OH) to afford product 23-8.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with 0.07 mL of water, 0.07 mL of 15% NaOH and 0.2 mL of water
  3. filtrationThe precipitate was filtered
  4. concentrationconcentrated
  5. custompurified by column chromatography (94:6:0.6 CHCl3 /IPA/NH4OH)

Sources & evidence

ORD record
ord-d647c51f051f4ae191a7d60ffc9701d0
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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