Benzyl Bromide → HCID 19366841, compound

HRID 849540Notes

Reaction equation

HRID 849540 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH2:15][CH2:16][CH2:17][OH:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].C([Li])CCC.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Cl-].[NH4+]>C1COCC1.CCCCCC.O.C(OCC)(=O)C.CN1C(=O)N(C)CCC1>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH:15]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:16][CH2:17][OH:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

10

Reactant 4

HCID 7498Benzyl BromideHCID 25517Ammonium ChlorideHCID 19366832HCID 19366832, compoundHCID 178418339Butyllithium

Product 1

HCID 19366841HCID 19366841, compoundYield 91.3%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

Part A: To a solution of 4.0 g (15 mmol) of 3-[(4-butoxyphenyl)sulfonyl]propan-1-ol from Example 26 and 6 mL of DMPU in 100 mL of anhydrous THF at -70 C under nitrogen, was added 3.9 mL (1.9 g, 29 mmol) of a 10.0 M solution of n-butyllithium in hexane. After stirring for 30 min. at -70 C., 1.6 mL (2.3 g, 13 mmole) of benzyl bromide was added. After 15 hours, the reaction mixture was cooled to zero C. and 25 mL of saturated ammonium chloride solution was added. Ethyl acetate and water were added, 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 8.4 g of crude product. This was chromatographed on silica gel using 25%-35% ethyl acetate/hexane to yield 4.3 g of pure 3-[(4-butoxyphenyl)sulfonyl]-4-phenylbutan-1-ol.

Workup

  1. waitAfter 15 hours
  2. temperaturethe reaction mixture was cooled to zero C
  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 8.4 g of crude product
  10. customThis was chromatographed on silica gel using 25%-35% ethyl acetate/hexane

Sources & evidence

ORD record
ord-636399faaeac4390b44be837d4a1d426
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

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