Hydrochloric Acid → HCID 83383390, compound

HRID 271299Notes

Reaction equation

HRID 271299 reaction equation
[Li]CCCC.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][CH:16]=[N:15][CH:14]=2)=[CH:9][CH:8]=1.CN([CH:21]=[O:22])C.Cl>C1COCC1.CCOCC>[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[O:17][C:16]([CH:21]=[O:22])=[N:15][CH:14]=2)=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 27374805-(4-Fluorophenyl)-1,3-oxazoleHCID 178418339Butyllithium

Product 1

HCID 83383390HCID 83383390, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of nBuLi (1.6 M in hexane, 3.45 ml, 5.53 mmol) was added dropwise at −78° C. to a stirred solution of 5-(4-fluorophenyl)-1,3-oxazole (0.82 g, 5.03 mmol) in THF (10 ml) (Organic Letters (2001),(3)2, 271-273). The mixture was stirred at −78° C. for 30 minutes and then quenched with DMF (0.43 ml, 5.53 mmol). It was gradually warmed to room temperature, stirred for further 30 minutes, diluted with Et2O (30 ml), then neutralised with 1N HCl. The organic layer was separated, washed with brine (20 ml), dried over MgSO4 and concentrated in vacuo. Purification by chromatography on silica gel eluting with DCM afforded 5-(4-fluorophenyl)-1,3-oxazole-2-carbaldehyde (0.58 g, 60%): δH (360 MHz, CDCl3) 7.18 (2H, t, J 8.6 ), 7.58 (1H, s), 7.77-7.81 (2H, m), 9.76 (1H, s); m/z (ES+) 192 (MH+).

Workup

  1. temperatureIt was gradually warmed to room temperature
  2. stirringstirred for further 30 minutes
  3. customThe organic layer was separated
  4. washwashed with brine (20 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography on silica gel eluting with DCM

Sources & evidence

ORD record
ord-15e4f32f68cb4bc8bfa540c78de69d04
Source dataset
uspto-grants-2008_11
Patent number
US07452899B2

Reaction notes

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