Aluminium lithium hydride → HCID 68529104, compound

HRID 1429299Notes

Reaction equation

HRID 1429299 reaction equation
[C:1]([N:20]1[C:24]([C:25](OC)=[O:26])=[C:23]([C:29](OC)=[O:30])[C:22]([C:33](OC)=[O:34])=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.CCOCC>[C:1]([N:20]1[C:24]([CH2:25][OH:26])=[C:23]([CH2:29][OH:30])[C:22]([CH2:33][OH:34])=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68531009HCID 68531009, compound

Product 1

HCID 68529104HCID 68529104, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22.5 °C

Procedure

To a solution of trimethyl 1-trityl-3,4,5-pyrazoletricarboxylate (3.034 g, 6.26 mmol) in dry THF (60 mL) were added 50 mL of 1.0 M LiAlH4 in Et2O. The resulting solution was stirred for about 16 h at room temperature (20-25° C.). After this time, the reaction was quenched by the slow addition of 1.5 mL of distilled water, followed by addition of 1.5 mL of 10% NaOH and 3.5 mL of water. The solids formed were removed by filtration, and 80 mL of dichloromethane was added to the filtrate. The organic phase was separated, washed with distilled water (70 mL) and, after separation from the aqueous phase, was dried over MgSO4. After separation of the organic phase, the solvent was evaporated under vacuum yielding a yellowish solid. Yield: 73% (1.823 g, 4.54 mmol).

Workup

  1. customAfter this time, the reaction was quenched by the slow addition of 1.5 mL of distilled water
  2. additionfollowed by addition of 1.5 mL of 10% NaOH and 3.5 mL of water
  3. customThe solids formed
  4. customwere removed by filtration, and 80 mL of dichloromethane
  5. additionwas added to the filtrate
  6. customThe organic phase was separated
  7. washwashed with distilled water (70 mL)
  8. customafter separation from the aqueous phase
  9. dry with materialwas dried over MgSO4
  10. customAfter separation of the organic phase
  11. customthe solvent was evaporated under vacuum
  12. customyielding a yellowish solid

Sources & evidence

ORD record
ord-9b16d714e6d04b2085c5a8df43c23f3b
Source dataset
uspto-grants-2015_01
Patent number
US08940273B2

Reaction notes

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