Diisobutylaluminumhydride → HCID 69737506, compound

HRID 2416535Notes

Reaction equation

HRID 2416535 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14](=O)/[C:15](/[F:29])=[CH:16]/[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[CH:19][CH:18]=1)C>C(Cl)Cl>[F:29]/[C:15](=[CH:16]\[C:17]1[CH:18]=[CH:19][C:20]([C:23]2[N:24]=[CH:25][CH:26]=[CH:27][N:28]=2)=[CH:21][CH:22]=1)/[CH2:14][OH:13]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 69728829HCID 69728829, compound

Product 1

HCID 69737506HCID 69737506, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Diisobutylaluminum hydride (1.0 M solution in THF, 5.5 mL, 5.50 mmol) was added dropwise to a 0° C. solution of the product from step A (500 mg, 1.84 mmol) in methylene chloride (15 mL). The resulting solution was stirred for 10 min at 0° C., quenched with methanol (0.25 mL) followed by 15% aq. Rochelle salt (20 mL), and allowed to stir at room temperature for 4 h. The layers were separated and the aqueous layer was extracted with methylene chloride (20 mL). The combined organic layers were dried (MgSO4) and concentrated to provide 415 mg (98%) of the title compound as a colorless solid. MS 231 (M+H)+.

Workup

  1. customquenched with methanol (0.25 mL)
  2. stirringto stir at room temperature for 4 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with methylene chloride (20 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fee6180ccbe04bf8ad3de45c2c46c686
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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