Diisobutylaluminumhydride → HCID 11131640, compound

HRID 1168099Notes

Reaction equation

HRID 1168099 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=2)=[C:7]([Cl:24])[CH:6]=1)C.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[Cl:11][C:9]1[CH:10]=[C:5]([CH2:4][OH:3])[CH:6]=[C:7]([Cl:24])[C:8]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 69755730HCID 69755730, compound

Product 1

HCID 11131640HCID 11131640, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-dichloro-4-(3-isopropyl-4-methoxy-phenoxy)-benzoic acid ethyl ester (prepared as described in Example 1, Step A) (100 mg, 0.26 mmol) in methylene chloride (3 mL) at −78° C. under nitrogen was added diisobutylaluminum hydride (1M in hexane, 0.6 ml, 0.6 mmol). The reaction mixture was warmed to room temperature and stirred for about 19 hours. The reaction was quenched with methanol (1 ml) and sodium potassium tartrate (0.5M aqueous solution, 2 ml). After stirring for about 15 minutes, the solution was extracted with methylene chloride (3×10 mL). The combined organic extracts were washed with saturated sodium bicarbonate and brine, dried, filtered, and concentrated. The crude product was purified by preparative TLC (methylene chloride) to afford the title compound (75 mg) as a solid. NMR (400 MHz, CDCl3) δ7.39 (s, 2H), 6.85 (d, 1H), 6.69 (d, 1H), 6.43-6.46 (dd, 1H), 4.68 (s, 2H), 3.77 (s, 3H), 3.26-3.30 (sept, 1H), 2.03 (bs, 1H), 1.18 (d, 6H).

Workup

  1. customThe reaction was quenched with methanol (1 ml) and sodium potassium tartrate (0.5M aqueous solution, 2 ml)
  2. stirringAfter stirring for about 15 minutes
  3. extractionthe solution was extracted with methylene chloride (3×10 mL)
  4. washThe combined organic extracts were washed with saturated sodium bicarbonate and brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by preparative TLC (methylene chloride)

Sources & evidence

ORD record
ord-1c1a3f9e396c43308a8071cbadf80b64
Source dataset
uspto-grants-2003_09
Patent number
US06620830B2

Reaction notes

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