Ethyl Bromide → HCID 19366851, compound

HRID 849529Notes

Reaction equation

HRID 849529 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH2:13][CH2:14]S)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C([Li])C[CH2:18][CH3:19].BrCC.[Cl-].[NH4+].C1C[O:29]CC1>CCCCCC.O.C(OCC)(=O)C.CN1C(=O)N(C)CCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]([CH2:18][CH3:19])[CH2:13][CH2:14][OH:29])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

10

Reactant 5

HCID 6332Ethyl BromideHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 18411961HCID 18411961, compoundHCID 178418339Butyllithium

Product 1

HCID 19366851HCID 19366851, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
-70 °C

Procedure

Part A: To a solution of 4.6 g (20 mmol) of 3-[(4-methoxyphenyl)sulfonyl]propane-1-ol from example 13 and 6 mL of DMPU in 60 mL of anhydrous THF at -70° C. under nitrogen, was added 5.8 mL (2.8 g, 44 mmol) of a 10.0 M solution of n-butyllithium in hexane. After stirring for 30 min. at -70° C., 1.6 mL (2.4 g, 22 mmole) of 1-bromoethane was added. After 2 hours, the reaction mixture was cooled to zero° C. and 25 mL of saturated ammonium chloride solution was added, followed by ethyl acetate and water, the layers were separated and the aqueous layer was extracted 2 ×s with ethyl acetate. The 3 organic layers were combined and washed with brine, dried with magnesium sulfate, filtered and concentrated to afford 4 g of crude product. This was chromatographed on silica gel using 40%-55% ethyl acetate/hexane to yield 2.4 g of pure 3-[(4-methoxyphenyl)sulfonyl]-pentan-1-ol, m/z=265 (M+Li).

Workup

  1. waitAfter 2 hours
  2. temperaturethe reaction mixture was cooled
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted 2 ×
  5. washwashed with brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford 4 g of crude product
  10. customThis was chromatographed on silica gel using 40%-55% ethyl acetate/hexane

Sources & evidence

ORD record
ord-4095b8ad36ff49c19caef15896e706c7
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

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