Diisobutylaluminum hydride → HCID 54756895, compound

HRID 1496921Notes

Reaction equation

HRID 1496921 reaction equation
CC(C[AlH]CC(C)C)C.[F:10][C:11]([F:32])([F:31])[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27](OC)=[O:28])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1>C1(C)C=CC=CC=1.C(Cl)Cl>[F:10][C:11]([F:31])([F:32])[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[CH2:27][OH:28])=[CH:21][CH:20]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 54757818methyl (2E)-3-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-2-propenoate

Product 1

HCID 54756895HCID 54756895, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

DIBAL-H (20% w/w in toluene, 2 mL, 2.39 mmol) was added to a slurry of ester 100 (0.396 g, 1.23 mmol) in toluene (12 mL) at −78° C. The mixture was warmed to room temperature, stirred for 1 h, and then poured onto ice cold NH4Cl solution (50 mL). The mixture was diluted with CH2Cl2 (100 mL), filtered through Celite and the organic layer was dried and evaporated. Column chromatography of the residue on silica gel using gradient elution (CH2Cl2 to 95:5 CH2Cl2:EtOAc) gave (2E)-3-[4′-(trifluoromethoxy)[1,1′-biphenyl]-4-yl]-2-propen-1-ol (101) (0.195 g, 54%) as a white solid: mp 121-123° C.; NMR (CDCI3) δ 7.60 (d, J=8.7 Hz, 2H), 7.53 (d, J=8.4 Hz, 2H), 7.47 (d, J=8.4 Hz, 2H), 7.28 (d, J=8.1 Hz, 2H), 6.66 (d, J=15.9 Hz, 1H), 6.42 (dt, J=15.9, 5.7 Hz, 1H), 4.36 (dd, J=5.9, 5.7 Hz, 2H), 1.44 (t, J=5.9 Hz, 1H). APCI MS m/z 307 [M−H−H2O+MeOH]−.

Workup

  1. additionpoured onto ice cold NH4Cl solution (50 mL)
  2. filtrationfiltered through Celite
  3. customthe organic layer was dried
  4. customevaporated
  5. washColumn chromatography of the residue on silica gel using gradient elution (CH2Cl2 to 95:5 CH2Cl2:EtOAc)

Sources & evidence

ORD record
ord-c07eba49b4614cf7b6ee845704a90bd9
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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