Tetrabutylammonium Fluoride → 2,8-Bis(trifluoromethyl)-alpha-(3-hydroxymethylphenyl)-4-quinolinemethanol

HRID 1370335Notes

Reaction equation

HRID 1370335 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:12]=[C:11]([CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:22][Si](C(C)(C)C)(C)C)[CH:16]=2)[OH:14])[C:10]2[C:5](=[C:6]([C:30]([F:33])([F:32])[F:31])[CH:7]=[CH:8][CH:9]=2)[N:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:34][C:2]([F:1])([F:35])[C:3]1[CH:12]=[C:11]([CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=2)[OH:14])[C:10]2[C:5](=[C:6]([C:30]([F:33])([F:32])[F:31])[CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 185114572,8-Bis(trifluoromethyl)-alpha-(3-tert-butyldimethylsilyloxymethylphenyl)-4-quinolinemethanol

Product 1

HCID 185114202,8-Bis(trifluoromethyl)-alpha-(3-hydroxymethylphenyl)-4-quinolinemethanolYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,8-bis(trifluoromethyl)-α-(3-tert-butyldimethylsilyloxymethylphenyl)-4-quinolinemethanol (crude, 1.17 mmol) in THF (5 mL) was treated with tetrabutylammonium fluoride (1-M in UHF, 0.7 mL, 0.7 mmol), stirred for 15 min, washed with water (2×2 mL), concentrated in vacuo and the resulting oil purified by chromatography [SiO2; heptane-EtOAc (3:1-1:1)] to give the title compound (117 mg, 25%) as a white solid: mp 152-154° C.; IR νmax (Nujol)/cm−1 3359, 3206, 2924, 1458, 1378, 1308, 1184, 1155, 1136, 1115, 1083, 1032, 766 and 695; NMR δH (400 MHz, CDCl3) 3.05 (1H, br s), 6.63 (2H, s), 6.48 (1H, s), 7.10-7.40 (4H, m), 7.68 (1H, m), 8.05-8.15 (2H, m), and 8.21 (1H, s).

Workup

  1. washwashed with water (2×2 mL)
  2. concentrationconcentrated in vacuo
  3. customthe resulting oil purified by chromatography [SiO2; heptane-EtOAc (3:1-1:1)]

Sources & evidence

ORD record
ord-e972490aa81b48c2a25df3e04b7181a6
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

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