Sodium Sulfate → HCID 89600966, compound

HRID 530243Notes

Reaction equation

HRID 530243 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[C:4]([C:10]#N)=[CH:3]1.[H-].C([Al+]CC(C)C)C(C)C.S([O-])([O-])(=O)=[O:24].[Na+].[Na+]>ClCCl>[CH3:1][C:2]1([CH3:12])[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[C:4]([CH:10]=[O:24])=[CH:3]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21225700DiisobutylaluminumhydrideHCID 89601219HCID 89601219, compound

Product 1

HCID 89600966HCID 89600966, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of the product of Example 10f (500 mg, 3.07 mmol) in dry dichloromethane (12.5 mL) at −78° C. was added diisobutyl aluminum hydride (6.5 mL, 6.14 mmol) and the reaction was warmed to room temperature and stirred for approximately 2.5 hours. Wet sodium sulfate was added to quench the reaction. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the title compound as a colorless oil. (360 mg, Yield: 71%). 1H NMR (400 MHz, CDCl3) δ 9.31 (s, 1H), 6.33 (s, 1H), 1.55-1.49 (m, 4H), 1.20 (s, 6H), 1.10 (s, 6H) ppm.

Workup

  1. customto quench
  2. customthe reaction
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-13932c337f0245e29f4bf8dc6f59a31f
Source dataset
uspto-grants-2016_05
Patent number
US09353063B2

Reaction notes

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