Diisobutylaluminum hydride → HCID 22057742, compound

HRID 1828695Notes

Reaction equation

HRID 1828695 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:14]([C:24]([F:27])([F:26])[F:25])[CH:13]=2)=[CH:6][CH:5]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[F:26][C:24]([F:25])([F:27])[C:14]1[CH:13]=[C:12]([S:11][CH2:10][C:7]2[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=2)[CH:17]=[CH:16][C:15]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 69135125HCID 69135125, compound

Product 1

HCID 22057742HCID 22057742, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-(2-trifluoromethyl-biphenyl-4-ylsulfanylmethyl)-benzoic acid methyl ester (83 mg, 0.2062 mmol, 1 eq.) in anhydrous toluene (5 mL) cooled to −78° C. is added DIBAL-H (1 M in toluene, 0.41 mL, 0.41 mmol, 2 eq). The mixture is stirred at −78° C. for 30 min. The reaction is quenched by the addition of saturated aqueous NH4Cl after which point the reaction mixture is allowed to warm to room temperature. The reaction is diluted with EtOAc and washed with 1 N HCl (aq), H2O, and saturated aqueous NaCl. The organic solution is dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (1:1 hexanes/EtOAc) to give [4-(2-trifluoromethyl-biphenyl-4-ylsulfanylmethyl)-phenyl]-methanol. [MS: (ES+) 397.1 (M+23)+].

Workup

  1. customThe reaction is quenched by the addition of saturated aqueous NH4Cl after which
  2. temperatureto warm to room temperature
  3. additionThe reaction is diluted with EtOAc
  4. washwashed with 1 N HCl (aq), H2O, and saturated aqueous NaCl
  5. dry with materialThe organic solution is dried over Na2SO4
  6. concentrationAfter concentration
  7. customthe residue is purified by silica gel chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-0db07425d6564a36a37010e76f41ef54
Source dataset
uspto-grants-2006_06
Patent number
US07060697B2

Reaction notes

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