4-Fluorophenol → HCID 12052043, compound

HRID 1594365Notes

Reaction equation

HRID 1594365 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[OH:11][CH2:12][C@@H:13]([N:15]1[C:19]([C:20]2[CH:25]=[CH:24][N:23]=[C:22](S(CCC)(=O)=O)[N:21]=2)=[C:18]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[N:17]=[CH:16]1)[CH3:14]>C1COCC1>[OH:11][CH2:12][C@@H:13]([N:15]1[C:19]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([O:10][C:7]3[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=3)[N:21]=2)=[C:18]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[N:17]=[CH:16]1)[CH3:14]

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 12052042HCID 12052042, compound

Product 1

HCID 12052043HCID 12052043, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

NaH (95%) (252 mg, 10 mmol) was added in small portions to absolution of 4-fluorophenol (2.21 g, 19.8 mmol) in dry THF (50 mL). After the vigorous reaction had subsided, this solution was added to a solution of the product of example 1 (g) (2 g, 4.95 mmol) dissolved in dry THF (200 mL). The reaction mixture was stirred at rt under argon for 1 h. The reaction mixture was concentrated, and the residue partitioned between EtOAc and H2O. The organic phase was washed with 1N NaOH, brine, dried (Na2SO4), and concentrated. The crude product was purified by flash chromatography (silica gel, 0–4% MeOH/CH2Cl2) to give the title compound as a light yellow solid. ES (+) MS m/e=409 (MH+)

Workup

  1. customAfter the vigorous reaction
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue partitioned between EtOAc and H2O
  4. washThe organic phase was washed with 1N NaOH, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (silica gel, 0–4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f01e813cf41e4cf6bf46142b5e9160f3
Source dataset
uspto-grants-2007_11
Patent number
US07301021B2

Reaction notes

Loading…