Ethyl Acetate → HCID 19366822, compound

HRID 849539Notes

Reaction equation

HRID 849539 reaction equation
[C:1]1([Mg]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH2:20][CH2:21][CH:22]=[O:23])(=[O:19])=[O:18])=[CH:13][CH:12]=1.[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1.O>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([S:17]([CH2:20][CH2:21][CH:22]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[OH:23])(=[O:18])=[O:19])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 19366861HCID 19366861, compoundHCID 178478979HCID 178478979, compound

Product 1

HCID 19366822HCID 19366822, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Part B: To 11.4 mL (3.2 g, 23 mM) of a 2.0 M phenylmagnesium chloride solution in THF at zero° C., was added 2.6 g (11 mmol) of 3-[(4-methoxyphenyl)sulfonyl]propan-1-al from Part A in 20 mL of THF. After 1.5 hours, the reaction mixture was cooled to zero° C. and 20 mL of saturated ammonium chloride solution was added, followed by ethyl acetate and water, the organic layer was separated and washed with 5% potassium hydrogen sulfate solution, saturated sodium bicarbonate solution and brine, dried with magnesium sulfate, filtered and concentrated to afford 2.7 grams of crude product. This was chromatographed on silica gel using 35%-40% ethyl acetate/hexane to yield 1.7 g of pure 3-[(4-methoxyphenyl)sulfonyl]-1-phenylpropan-1-ol, m/z=324 (M+NH4).

Workup

  1. temperaturethe reaction mixture was cooled
  2. customthe organic layer was separated
  3. washwashed with 5% potassium hydrogen sulfate solution, saturated sodium bicarbonate solution and brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford 2.7 grams of crude product
  8. customThis was chromatographed on silica gel using 35%-40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c407ad8109ca4b8d928e1117136034bc
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

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