Water → HCID 11698408, compound

HRID 1452697Notes

Reaction equation

HRID 1452697 reaction equation
[CH3:1][O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][O:13][C:14]2[C:19]([CH3:20])=[CH:18][C:17]([C:21]([O:30]CC3C=CC(OC)=CC=3)([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])=[CH:16][C:15]=2[CH3:40])=[CH:6][CH:5]=1.ClC(Cl)C.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.O>ClCCl.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:41])[C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][CH2:12][O:13][C:14]2[C:15]([CH3:40])=[CH:16][C:17]([C:21]([OH:30])([C:22]([F:23])([F:24])[F:25])[C:26]([F:28])([F:29])[F:27])=[CH:18][C:19]=2[CH3:20])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 63651,1-DichloroethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86604227HCID 86604227, compound

Product 1

HCID 11698408HCID 11698408, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To 105 mg (0.2 mmol) of 4-(2-{2,6-dimethyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethoxy)-benzoic acid methyl ester in 5 mL of dichloroethane 61 mg (0.3 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) and evaporated. Column chromatography on ISOLUTE Flash NH2 with EtOAc/n-heptane 1:1 gave 21 mg (25%) of 4-{2-[2,6-dimethyl-4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-benzoic acid methyl ester as a light yellow solid, MS: 465 (M−H)−.

Workup

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

Sources & evidence

ORD record
ord-91482475fca441f8b4871b320c77e72f
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

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