Acetic Acid → HCID 86626799, compound

HRID 604041Notes

Reaction equation

HRID 604041 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][O:8][CH:9]2O)=[CH:5][CH:4]=1.[F:15][C:16]([F:30])([F:29])[C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:20][NH2:21].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClCCCl.C(OCC)(=O)C>[F:15][C:16]([F:29])([F:30])[C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([C:25]([F:28])([F:26])[F:27])[CH:24]=1)[CH2:20][NH:21][CH2:9][C:10]1[CH:11]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=[CH:5][C:6]=1[CH2:7][OH:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 67087230HCID 67087230, compound

Product 1

HCID 86626799HCID 86626799, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Trifluoromethyl-1,3-dihydro-isobenzofuran-1-ol (4.12 g) is dissolved in 1,2-dichloroethane (75 ml), and thereto are added 3,5-bis-trifluoromethyl-benzylamine (5.89 g), triacetoxy-sodium borohydride (9.0 g) and acetic acid (2.3 ml), and the mixture is stirred at room temperature for 1 hour. To the reaction solution are added a saturated aqueous sodium bicarbonate 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=7:3→1:1) to give {2-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-4-trifluoromethyl-phenyl}-methanol (7.06 g). MS (m/z): 432 [M+H]+

Workup

  1. customthe mixture is separated
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=7:3→1:1)

Sources & evidence

ORD record
ord-9d8c69cfb8ea4299ae281ddfc3a00f1b
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

Loading…