Diisobutylaluminumhydride → HCID 58504153, compound

HRID 2407832Notes

Reaction equation

HRID 2407832 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[S:10][C:11]([C:18](OCC)=[O:19])=[C:12]([CH2:14][N:15]([CH3:17])[CH3:16])[N:13]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[S:10][C:11]([CH:18]=[O:19])=[C:12]([CH2:14][N:15]([CH3:16])[CH3:17])[N:13]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 58503950HCID 58503950, compound

Product 1

HCID 58504153HCID 58504153, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound prepared in Example 439 (12.5 g) in dichloromethane (300 mL) at −95° C. was added a 1 mol/L solution of diisobutylaluminium hydride (48.5 mL) in hexanes dropwise slowly. The mixture was stirred for 3 hours and then quenched with methanol (50 mL). A solution of Rochelle's salt was then added dropwise. The mixture was warmed to room temperature and extracted with ethyl acetate. The combined extracts were washed with water and then concentrated. The residue was purified by column chromatography on silica gel (petroleum ether:ethyl acetate=5:1) to obtain the title compound (4.3 g) having the following physical data.

Workup

  1. customquenched with methanol (50 mL)
  2. additionA solution of Rochelle's salt was then added dropwise
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with water
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-24afe96a9483409dbb86e47347db65bd
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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