Diisobutylaluminumhydride → HCID 21867456, compound

HRID 857311Notes

Reaction equation

HRID 857311 reaction equation
[Br:1][C:2]1[N:3]([CH2:19][CH2:20][CH2:21][C:22](OCC)=[O:23])[C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Br:1][C:2]1[N:3]([CH2:19][CH2:20][CH2:21][CH:22]=[O:23])[C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 21867387HCID 21867387, compound

Product 1

HCID 21867456HCID 21867456, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a vigorously stirred solution of 0.3 g of the product from Step 3 in 5 mL of THF cooled at −78° C. was added dropwise a solution of diisobutylaluminum hydride (4 mL, 1 M in hexane). After stirring for 30 minutes at −78° C., the reaction was quenched with 1 mL of acetone followed by 10 mL of 20% aqueous solution of potassium sodium tartrate. The mixture was extracted with 20 mL of 1:1 hexane/EtOAc and the extract was dried over Na2SO4 and concentrated. The residue was purified by silica gel flash chromatography eluted with 8:1 hexane/EtOAc to give 0.19 g of the title compound as an oil.

Workup

  1. customthe reaction was quenched with 1 mL of acetone
  2. extractionThe mixture was extracted with 20 mL of 1:1 hexane/EtOAc
  3. dry with materialthe extract was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluted with 8:1 hexane/EtOAc

Sources & evidence

ORD record
ord-84929537fda24fbc9fa29258d89050b8
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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