Trifluoroacetic acid → 2-(3-Fluorophenyl)chroman-6-ol

HRID 31175Notes

Reaction equation

HRID 31175 reaction equation
C([SiH](CC)CC)C.[F:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:24][CH:23](O)[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([OH:26])[CH:21]=3)[O:16]2)[CH:12]=[CH:13][CH:14]=1.FC(F)(F)C(O)=O>ClCCl>[F:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:24][CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([OH:26])[CH:21]=3)[O:16]2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 179786382-(3-Fluorophenyl)chroman-4,6-diol

Product 1

HCID 179784712-(3-Fluorophenyl)chroman-6-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylsilane (960 μl) was added slowly into a solution of 2-(3-fluorophenyl)chroman-4,6-diol (195 mg) in dichloromethane (4 ml). Trifluoroacetic acid (1.9 ml) was then added dropwise into a reaction mixture and it was stirred at room temperature for 5 hours. The reaction mixture was poured on ice-water and extracted with dichloromethane. The residue was evaporated under reduced pressure with toluene to obtain 2-(3-fluorophenyl)chroman-6-ol. 1H NMR (400 MHz, d6-DMSO) δ: 8.78 (s, 1H), 7.43 (m, 1H), 7.28-7.25 (m, 2H), 7.14 (m, 1H), 6.66 (d, 1H, J 8.5 Hz) 6.52 (dd, 1H, J 8.5, 2.7 Hz), 6.49 (d, 1H, J 2.7 Hz), 5.03 (dd, 1H, J 9.9, 2.1 Hz), 2.86 (m, 1H), 2.63 (m, 1H), 2.13 (m, 1H), 1.93 (m, 1H).

Workup

  1. additionThe reaction mixture was poured on ice-water
  2. extractionextracted with dichloromethane
  3. customThe residue was evaporated under reduced pressure with toluene

Sources & evidence

ORD record
ord-b8a385ba1d5441ee9dd4170227d87e51
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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