Ammonium Chloride → HCID 17989149, compound

HRID 1443227Notes

Reaction equation

HRID 1443227 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][CH3:18])[CH:11]=1)([CH3:9])[CH3:8])[CH3:2].C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:27])C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([OH:27])[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][CH3:18])[CH:11]=1)([CH3:8])[CH3:9])[CH3:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 17989120HCID 17989120, compound

Product 1

HCID 17989149HCID 17989149, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

24.1 g (84.63 mmol) of ethyl-4-(4-chloro-3-methoxyphenyl)-4-methylpentanoate is dissolved in 296 ml of tetrahydrofuran, and the reaction mixture is cooled to −70° C. to −65° C. Within ¾ hour, 236.9 ml of a 0.5 molar solution of potassium-bis-(trimethylsilylamide) in toluene is added in drops, and the reaction mixture is then stirred for 75 more minutes at −70° C. 30.9 g (118.48 mmol) of Davis reagent, dissolved in 296 ml of tetrahydrofuran, is now added in drops within 60 minutes. After two hours of stirring at −70° C., 152 ml of saturated ammonium chloride solution is slowly added in drops, the cold bath is removed, and it is stirred vigorously for thirty minutes. After extraction with diethyl ether, the combined organic extracts are treated as usual with water and brine. After the solvent is spun off, the residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane). 21.4 g (84.2%) of the desired compound (slightly contaminated) is isolated.

Workup

  1. temperaturethe reaction mixture is cooled to −70° C. to −65° C
  2. waitWithin ¾ hour
  3. additionis now added in drops within 60 minutes
  4. stirringAfter two hours of stirring at −70° C.
  5. customthe cold bath is removed
  6. stirringit is stirred vigorously for thirty minutes
  7. extractionAfter extraction with diethyl ether
  8. additionthe combined organic extracts are treated as usual with water and brine
  9. customthe residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane)
  10. customis isolated

Sources & evidence

ORD record
ord-39e973a6bd87490f99b6147ca03e361e
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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