Ammonium Chloride → Ethyl-4-(3-methoxyphenyl)-2-hydroxy-4-methylpentanoate

HRID 1443269Notes

Reaction equation

HRID 1443269 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)([CH3:9])[CH3:8])[CH3:2].C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:26])C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([OH:26])[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)([CH3:8])[CH3:9])[CH3:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 17989275Ethyl-4-(3-methoxyphenyl)-4-methylpentanoate

Product 1

HCID 17989103Ethyl-4-(3-methoxyphenyl)-2-hydroxy-4-methylpentanoateYield 72.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

27.2 g (108.65 mmol) of ethyl-4-(3-methoxyphenyl)-4-methylpentanoate is dissolved in 380 ml of tetrahydrofuran, and the reaction mixture is cooled to −70° C. to −65° C. Within two hours, 304 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. 39.7 g (152.11 mmol) of Davis reagent, dissolved in 380 ml of tetrahydrofuran, is now added in drops within 90 minutes. After two hours of stirring at −70° C., 195 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 (twice with 800 ml each), 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). 20.9 g (72.4%) of the desired compound is isolated.

Workup

  1. temperaturethe reaction mixture is cooled to −70° C. to −65° C
  2. additionis now added in drops within 90 minutes
  3. stirringAfter two hours of stirring at −70° C.
  4. customthe cold bath is removed
  5. stirringit is stirred vigorously for thirty minutes
  6. extractionAfter extraction with diethyl ether (twice with 800 ml each), the combined organic extracts
  7. additionare treated as usual with water and brine
  8. customthe residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-83dfe63b05094017beb8870317e01807
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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