Ethanol → HCID 18511424, compound

HRID 1370339Notes

Reaction equation

HRID 1370339 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:12]=[C:11]([CH2:13][C:14](=O)[CH2:15][CH2:16][OH:17])[C:10]2[C:5](=[C:6]([C:19]([F:22])([F:21])[F:20])[CH:7]=[CH:8][CH:9]=2)[N:4]=1.[BH4-].[Na+].CC[OH:29]>O>[F:1][C:2]([F:23])([F:24])[C:3]1[CH:12]=[C:11]([CH:13]([OH:29])[CH2:14][CH2:15][CH2:16][OH:17])[C:10]2[C:5](=[C:6]([C:19]([F:21])([F:22])[F:20])[CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 86759029HCID 86759029, compound

Product 1

HCID 18511424HCID 18511424, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-(2,8-bis(trifluoromethyl)-4-quinolinyl)-4-hydroxybutanone (748 mg, 2.13 mmol) in EtOH (4 mL) at 0° C. was treated with a solution of NaBH4 (81 mg, 2.13 mmol) in water (0.2 mL), stirred at 0° C. for 30 min, poured into water (15 mL), extracted with EtOAc (2×10 mL),dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; EtOAc-heptane (2:1)] to give the title compound (618 mg, 82%) as a colourless oil; IR νmax (Nujol)/cm−1 3600-3200, 2938, 2885, 1604,1588, 1430, 1310, 1189, 1144 and 1110; NMR δH (400 MHz, CDCl3) 1.81-1.91 (3H, m), 2.08-2.17 (1H, m), 2.45-2.70 (2H, br s),3.75-3.78 (1H, m), 3.80-3.88 (1H, m), 5.52 (1H, d, J 8.0 Hz), 7.71 (1H, t, J 7.9 Hz), 8.08 (1H, s), 8.15 (1H, d, J 7.2 Hz) and 8.23 (1H, d, J 8.7 Hz).

Workup

  1. extractionextracted with EtOAc (2×10 mL),dried (MgSO4),
  2. concentrationconcentrated in vacuo
  3. custompurified by chromatography [SiO2; EtOAc-heptane (2:1)]

Sources & evidence

ORD record
ord-7b89264b91ea48c192345de6bd55471d
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

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