Water → Rac 4-{2-phenyl-2-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-benzaldehyde

HRID 1452703Notes

Reaction equation

HRID 1452703 reaction equation
[C:1]1([CH:7]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:34]CC3C=CC(OC)=CC=3)([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=2)[CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(Cl)C.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.O>ClCCl.CCOC(C)=O>[C:1]1([CH:7]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([OH:34])([C:30]([F:31])([F:32])[F:33])[C:26]([F:28])([F:29])[F:27])=[CH:21][CH:20]=2)[CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH:14]=[O:15])=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 63651,1-DichloroethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 87604503Rac 4-(2-phenyl-2-{4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethoxy)-benzaldehyde

Product 1

HCID 87604907Rac 4-{2-phenyl-2-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-benzaldehydeYield 64.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To 44 mg (0.07 mmol) of rac 4-(2-phenyl-2-{4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethoxy)-benzaldehyde in 2 mL of dichloroethane 33 mg (0.15 mmol) of DDQ and a drop of water were added. The reaction mixture was stirred at 70° C. overnight, cooled to room temperature and was diluted with dichloromethane and EtOAc, dried (Na2SO4), filtered and evaporated. Column chromatography on silica gel with EtOAc/n-heptane 1:5 gave 22 mg (62%) of rac 4-{2-phenyl-2-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-benzaldehyde, MS: 483 (M−H)−.

Workup

  1. temperaturecooled to room temperature
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-ee6562bdd8364dfe9d7b715e977ab8a4
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

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