Toluene → HCID 68459332, compound

HRID 502409Notes

Reaction equation

HRID 502409 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[C:8]([O:22][CH2:23][CH3:24])[CH:7]=1)=O)C.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1>C1COCC1>[CH2:23]([O:22][C:8]1[CH:7]=[C:6]([CH2:4][OH:3])[CH:11]=[CH:10][C:9]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=1)[CH3:24]

Participants

5

Reactant 3

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 68458497HCID 68458497, compound

Product 1

HCID 68459332HCID 68459332, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the above synthesized 2-ethoxy-4′-trifluoromethyl-biphenyl-4-carboxylic acid ethyl ester (0.515 g, 1.52 mmol), dissolved in 6 ml of abs. THF, was added drop wise at −10° C. DIBAL-H solution in toluene (3.81 ml 1M, 2.5 eq.). After additional 60 Min. at ambient temperature, the reaction mixture was carefully poured onto crashed ice/dil. HCl-solution, twofold extracted with AcOEt, washed with water, dried over sodium sulfate, and evaporated to dryness. Thereby, 0.359 g of the title alcohol was isolated as white solid, sufficiently pure for the next step.

Workup

  1. dissolutiondissolved in 6 ml of abs
  2. additionat ambient temperature, the reaction mixture was carefully poured
  3. extractionHCl-solution, twofold extracted with AcOEt
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-7ae22ee860e84881a9b9f869c7832d53
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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