Dimethylformamide → HCID 86675605, compound

HRID 1519232Notes

Reaction equation

HRID 1519232 reaction equation
Br[C:2]1[N:3]=[C:4]([CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[O:5][C:6]=1[S:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.[Li]CCCC.CN([CH:29]=[O:30])C>C1COCC1>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([S:7][C:6]2[O:5][C:4]([CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[N:3][C:2]=2[CH:29]=[O:30])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67451842HCID 67451842, compoundHCID 178418339Butyllithium

Product 1

HCID 86675605HCID 86675605, compoundYield 118.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a dry flask was added 4-bromo-5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole (810 mg, 2.162 mmol) and THF (21.6 mL), and the reaction mixture was cooled to 78° C. nBuLi (1.486 mL, 2.378 mmol) was added slowly and the reaction mixture was stirred at −78° C. for 5 min. DMF (0.837 mL, 10.81 mmol) was added and the reaction mixture was stirred at −78° C. for 10 min, quenched with water, allowed to warm to RT. The reaction mixture was extracted with EtOAc, washed with 3M LiCl, dried over sodium sulfate and concentrated in vacuo to give 5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole-4-carbaldehyde (830 mg crude) to be used as is in the next step. MS: M+H=324.

Workup

  1. additionwas added slowly
  2. stirringthe reaction mixture was stirred at −78° C. for 10 min
  3. customquenched with water
  4. temperatureto warm to RT
  5. extractionThe reaction mixture was extracted with EtOAc
  6. washwashed with 3M LiCl
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e0e8e74e28b48508180814d40b070fe
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

Loading…