Tetrahydrofuran → HCID 58757367, compound

HRID 916698Notes

Reaction equation

HRID 916698 reaction equation
C[Mg]I.[CH2:4]([N:6]1[C:10]([C:11]2[CH:12]=[C:13]([C:17]([NH:20][S:21]([CH2:24][C:25]([F:28])([F:27])[F:26])(=[O:23])=[O:22])([CH3:19])[CH3:18])[CH:14]=[CH:15][CH:16]=2)=[CH:9][C:8]([CH:29]=[O:30])=[N:7]1)[CH3:5].[CH2:31]1COCC1>CCOCC>[CH2:4]([N:6]1[C:10]([C:11]2[CH:12]=[C:13]([C:17]([NH:20][S:21]([CH2:24][C:25]([F:26])([F:27])[F:28])(=[O:23])=[O:22])([CH3:19])[CH3:18])[CH:14]=[CH:15][CH:16]=2)=[CH:9][C:8]([CH:29]([OH:30])[CH3:31])=[N:7]1)[CH3:5]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 58757371HCID 58757371, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 58757367HCID 58757367, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of MeMgI (1.47 mmol) in Et2O (3.0 M, 0.49 mL) was added dropwise over 2 min to a stirred mixture of the aldehyde from Step 1 and THF (10 mL) at 0° C. under N2. The reaction mixture was stirred for 15 min and then quenched by the addition of NH4Cl solution (15 mL). The organics were extracted into EtOAc (40 mL), concentrated under reduced pressure, and purified by column chromatography on silica, eluting with 80% EtOAc/iso-hexane to yield the alcohol (121 mg, 58%). 1H NMR (CDCl3, 400 MHz) δ 7.60-7.45 (3H, m), 7.35 (1H, d, J=7.6 Hz), 6.23 (1H, s), 5.08 (1H, s), 4.98 (1H, q, J=6.5 Hz), 4.15-4.07 (2H, m), 3.53-3.42 (2H, m), 1.82 (6H, s), 1.57 (3H, d, J=6.5 Hz), 1.39 (3H, t, J=7.2 Hz). MS (ES+) C18H24F3N3O3S requires: 419, found: 420 (M+H+, 100%).

Workup

  1. customquenched by the addition of NH4Cl solution (15 mL)
  2. extractionThe organics were extracted into EtOAc (40 mL)
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography on silica
  5. washeluting with 80% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-b8d455fde860424b9b628fe03badcb75
Source dataset
uspto-grants-2007_09
Patent number
US07271191B2

Reaction notes

Loading…