Diisobutylaluminum hydride → HCID 11482932, compound

HRID 1169283Notes

Reaction equation

HRID 1169283 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:9]#[N:10])=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.B.C1COCC1.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:9][NH2:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 2723981Borane;tetrahydrofuranHCID 11346467HCID 11346467, compound

Product 1

HCID 11482932HCID 11482932, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of Example 1A (1.5 g, 5.4 mmol) in toluene (15 mL) at room temperature was treated dropwise with 1M DIBAL-H in toluene (5.4 mL, 5.4 mmol). After TLC showed complete consumption of the starting material, the concentrate was dissolved in THF (20 mL), treated with 1M BH3.THF (11.0 mL, 11.0 mmol), stirred for 2 hours, treated dropwise with saturated NH4Cl, stirred for 2 hours, and partitioned between dichloromethane and saturated NaHCO3. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated to provide the desired product.

Workup

  1. customconsumption of the starting material
  2. dissolutionthe concentrate was dissolved in THF (20 mL)
  3. stirringstirred for 2 hours
  4. custompartitioned between dichloromethane and saturated NaHCO3
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1942d9f139f8405dac16e289da2ce799
Source dataset
uspto-grants-2003_09
Patent number
US06627767B2

Reaction notes

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