Ethyl Acetate → HCID 67087230, compound

HRID 604040Notes

Reaction equation

HRID 604040 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][O:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].C(OCC)(=O)C>C(Cl)Cl.C1(C)C=CC=CC=1>[F:14][C:2]([F:1])([F:13])[C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][O:8][CH:9]2[OH:12])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 110744416-(Trifluoromethyl)isobenzofuran-1(3H)-oneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 67087230HCID 67087230, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

6-Trifluoromethyl-3H-isobenzofuran-1-one (1.77 g) is dissolved in methylene chloride (20 ml) and the mixture is cooled to −78° C., and thereto is added a 1.0M diisobutylaluminum hydride in toluene (19.5 ml) and the mixture is stirred for 1 hour and 20 minutes. The reaction solution is cooled to room temperature, and thereto are added a saturated aqueous ammonium chloride solution and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→3:2) to give 6-trifluoromethyl-1,3-dihydro-isobenzofuran-1-ol (1.36 g). MS (m/z): 187 [M+H—H2O]+

Workup

  1. temperatureThe reaction solution is cooled to room temperature
  2. customthe mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→3:2)

Sources & evidence

ORD record
ord-f9ac1c69357c4a84b40745246a9aedff
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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