Hydrochloric Acid → HCID 59517385, compound

HRID 1161481Notes

Reaction equation

HRID 1161481 reaction equation
N1CCOCC1.C([Li])CCC.Br[C:13]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])=[CH:17][C:14]=1[CH:15]=[O:16].[F:34]NS(C1C=CC=CC=1)(=O)=O.Cl>C1COCC1.C(OCC)C>[F:34][C:13]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])=[CH:17][C:14]=1[CH:15]=[O:16]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 15373214N-FluorobenzenesulfonamideHCID 59516832HCID 59516832, compoundHCID 178418339Butyllithium2×

Product 1

HCID 59517385HCID 59517385, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-40 °C

Procedure

To a solution of 2.01 ml of morpholine in 50 ml of THF there was added 8.69 ml of n-butyllithium (2.66 M, hexane solution) at −78° C. under a nitrogen atmosphere, and the mixture was stirred at −40° C. for 30 minutes. A solution of 2-bromo-4-methoxy-5-triisopropylsilanyloxybenzaldehyde in 15 ml of THF was then added dropwise at −78° C., and the mixture was further stirred at −78° C. for 40 minutes. After further adding 11.1 ml of n-butyllithium (2.66 M, hexane solution) at −78° C., the mixture was stirred at −78° C. for 40 minutes, and then a solution of 10.6 g of N-fluorobenzenesulfonamide in 40 ml of THF was added dropwise at −78° C. and the reaction mixture was stirred overnight while raising the temperature to room temperature. Dilute hydrochloric acid was added to the reaction mixture, and extraction was performed with diethyl ether. The organic layer was washed with saturated aqueous sodium hydrogencarbonate, water and saturated brine and then dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (2.96 g) as a light yellow solid.

Workup

  1. stirringthe mixture was further stirred at −78° C. for 40 minutes
  2. stirringthe mixture was stirred at −78° C. for 40 minutes
  3. stirringthe reaction mixture was stirred overnight
  4. temperaturewhile raising the temperature to room temperature
  5. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate, water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe desiccating agent was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-7c27cd58c00d4fb28630f319187e28be
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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