Diisobutylaluminumhydride → HCID 86607634, compound

HRID 1990894Notes

Reaction equation

HRID 1990894 reaction equation
FCC[O:4][C:5](=O)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([O:13][CH2:14][CH2:15][F:16])[CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][OH:4])=[CH:7][C:8]=1[O:13][CH2:14][CH2:15][F:16]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86607635HCID 86607635, compound

Product 1

HCID 86607634HCID 86607634, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-3-(2-fluoro-ethoxy)-benzoic acid 2-fluoro-ethyl ester (1.57 g, 5.93 mmol, 1.0 equiv) in anhydrous THF (30 mL) was added slowly over a time period of 15 min under cooling to −10° C. a solution of diisobutylaluminium hydride (17.8 mL, 17.80 mmol, 3.0 equiv; 1 M solution in toluene). After 1 h, the reaction mixture was poured on ice, extracted with ethyl acetate (2×100 mL) and the combined organic phases washed with water (2×100 mL). The organic phase was dried over Na2SO4, concentrated by evaporation under reduced pressure and the crude reaction product purified with column chromatography on silica eluting with hexane/ethyl acetate (2:3) to give 1.19 g (98%) of the title compound.

Workup

  1. additionthe reaction mixture was poured on ice
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washthe combined organic phases washed with water (2×100 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customthe crude reaction product
  7. custompurified with column chromatography on silica eluting with hexane/ethyl acetate (2:3)

Sources & evidence

ORD record
ord-78a66d7e1e784c5d87c4f78a635ced48
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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