Diisobutylaluminumhydride → HCID 68510790, compound

HRID 1715153Notes

Reaction equation

HRID 1715153 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:8]([O:19][CH2:20][CH3:21])[CH:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH2:20]([O:19][C:8]1[CH:7]=[C:6]([CH2:4][OH:3])[CH:11]=[CH:10][C:9]=1[C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)[CH3:21]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 68507568HCID 68507568, compound

Product 1

HCID 68510790HCID 68510790, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-ethoxy-4′-fluoro-biphenyl-4-carboxylic acid ethyl ester (0.50 g, 1.73 mmol, 1.0 equiv) in anhydrous THF (10 mL) was added dropwise at −10° C. diisobutylaluminum hydride (5.2 mL, 5.20 mmol, 3.0 equiv; 1 M solution in hexane) and the ccolong bath removed. After stirring for an additional time period of 60 min at rt, the reaction mixture was carefully poured on crashed ice/diluted HCl, extracted twice with ethyl acetate, the combined organic phases washed with water and a sat. solution of NaCl, dried over MgSO4 and concentrated by evaporation under reduced pressure. The title compound was isolated in quantitative yield (0.43 g) as a colorless viscous oil, sufficiently pure for the next step. MS (ISP): 229.3 [M+H−H2O]1.

Workup

  1. customthe ccolong bath removed
  2. additionthe reaction mixture was carefully poured
  3. extractionextracted twice with ethyl acetate
  4. washthe combined organic phases washed with water
  5. dry with materiala sat. solution of NaCl, dried over MgSO4
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-c04050c6a2284c0d8f132fe59b8dff13
Source dataset
uspto-grants-2010_09
Patent number
US07799806B2

Reaction notes

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