3-Pentanol → HCID 22249119, compound

HRID 349186Notes

Reaction equation

HRID 349186 reaction equation
[H-].[Na+].[CH3:3][CH2:4][CH:5]([OH:8])[CH2:6][CH3:7].Br[C:10]1[N:11]=[C:12]([O:31][CH3:32])[C:13]([C:18]2[CH:28]=[CH:27][C:21]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:20][C:19]=2[O:29][CH3:30])=[N:14][C:15]=1[CH2:16][CH3:17]>C1COCC1>[CH2:16]([C:15]1[N:14]=[C:13]([C:18]2[CH:28]=[CH:27][C:21]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:20][C:19]=2[O:29][CH3:30])[C:12]([O:31][CH3:32])=[N:11][C:10]=1[O:8][CH:5]([CH2:6][CH3:7])[CH2:4][CH3:3])[CH3:17]

Participants

5

Reactant 3

HCID 114283-PentanolHCID 24758Sodium hydrideHCID 22248930[4-(5-Bromo-6-ethyl-3-methoxypyrazin-2-yl)-3-methoxyphenoxy]trifluoromethane

Product 1

HCID 22249119HCID 22249119, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60% Sodium hydride (12 mg, 0.3 mmol) is added to a stirred solution of 3-pentanol (88 mg, 1 mmol) in THF (1 mL). After 0.5 hours [4-(5-bromo-6-ethyl-3-methoxypyrazin-2yl)-3-methoxyphenoxy]trifluoromethane (41 mg, 0.1 mmol) is added. The mixture is heated to 50 C for 12 hours, cooled and partitioned between ethyl acetate and water. The organic layer is washed with water, brine, dried (sodium sulfate), filtered and concentrated. The residue is purified by preparative TLC eluting with 50% ether in hexanes to give {4-[6-Ethyl-5-(ethylpropoxy)-3-methoxypyrazin-2-yl]-3-methoxyphenoxy}trifluoromethane, a colorless oil (19 mg). NMR (CDCL3, 400 MHz) δ 0.98 (t, 6H), 1.22 (t, 3H), 1.78 (m, 4H) 2.80 (q, 2H), 3.80 (s, 3H), 3.88 (s, 3H), 5.05 (quintet, 1H), 6.8 (s, 1H), 6.90 (d, 1H), 7.37 (d, 1H); MS 345 (M+1).

Workup

  1. temperatureThe mixture is heated to 50 C for 12 hours
  2. temperaturecooled
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer is washed with water, brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by preparative TLC
  9. washeluting with 50% ether in hexanes

Sources & evidence

ORD record
ord-86aa17ee3a764762867e0c6847d746b9
Source dataset
uspto-grants-2007_02
Patent number
US07179807B2

Reaction notes

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