Ethyl Acetate → HCID 19366810, compound

HRID 849537Notes

Reaction equation

HRID 849537 reaction equation
[CH2:1]([Mg]Cl)[CH2:2][CH2:3][CH3:4].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH2:18][CH2:19][CH:20]=[O:21])(=[O:17])=[O:16])=[CH:11][CH:10]=1.[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1.O>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([S:15]([CH2:18][CH2:19][CH:20]([OH:21])[CH2:1][CH2:2][CH2:3][CH3:4])(=[O:16])=[O:17])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 19366861HCID 19366861, compoundHCID 178418265HCID 178418265, compound

Product 1

HCID 19366810HCID 19366810, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Part B: To 22.3 mL (4.3 g, 37 mM) of a 2.0 M butylmagnesium chloride solution in THF at zero° C., was added 4.1 g (18 mmol) of 3-[(4-methoxyphenyl)sulfonyl]propan-1-al from Part A in 30 mL of THF. After 3 hours, the reaction mixture was cooled to zero° C. and 40 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 4.7 grams of crude product. This was chromatographed on silica gel using 30%-40% ethyl acetate/hexane to yield 3.1 g of pure 1-[(4-methoxyphenyl)sulfonyl]-heptan-3-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 4.7 grams of crude product
  8. customThis was chromatographed on silica gel using 30%-40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-1e12bda6346e4292b521caf6ebe92b22
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

Loading…