HCID 66707351, compound → HCID 66707167, compound

HRID 1496933Notes

Reaction equation

HRID 1496933 reaction equation
[F:1][C:2]([F:23])([F:22])[O:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[CH:21]=[CH:20][C:15]([C:16](OC)=[O:17])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1>CCOCC>[F:1][C:2]([F:22])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[CH:21]=[CH:20][C:15]([CH2:16][OH:17])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 66707351HCID 66707351, compound

Product 1

HCID 66707167HCID 66707167, compoundYield 120.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

LiAH4 (0.039 g, 1.03 mmol) was added to a solution of ester 126 (0.166 g, 0.515 mmol) in Et2O (10 mL) at 0° C. The mixture was stirred at room temperature for 0.5 h, and then cooled to 0° C., quenched with ice, and filtered through Celite. The organic fraction was dried and evaporated, and then column chromatography of the residue, eluting with 95:5 CH2Cl2:MeOH, gave (4-{(E)-2-[4-(trifluoromethoxy)phenyl]ethenyl}phenyl)methanol (127) (0.182 g, 82%) as a white solid: mp 161-163° C.; 1H NMR [(CD3)2SO] δ 7.78 (d, J=8.8 Hz, 2H), 7.57 (d, J=8.2 Hz, 2H), 7.31-7.38 (m, 4H), 7.27 (s, 2H), 5.16 (t, J=5.7 Hz, 1H), 4.51 (d, J=5.7 Hz, 2H). APCI MS m/z 277 [M+H−H2O]+.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with ice
  3. filtrationfiltered through Celite
  4. customThe organic fraction was dried
  5. customevaporated
  6. washcolumn chromatography of the residue, eluting with 95:5 CH2Cl2

Sources & evidence

ORD record
ord-99cd5aaa717b43d69a48a5ec0948834c
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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