Benzyl Bromide → HCID 19366823, compound

HRID 849530Notes

Reaction equation

HRID 849530 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])CCC.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+].C1C[O:34]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]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13][CH2:14][OH:34])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

10

Reactant 5

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 18411961HCID 18411961, compoundHCID 178418339Butyllithium

Product 1

HCID 19366823HCID 19366823, 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 5.0 g (22 mmol) of 3-[(4-methoxyphenyl)sulfonyl]propan-1-ol from example 13 and 6 mL of DMPU in 100 mL of anhydrous THF at -70° C. under nitrogen, was added 5.7 mL (2.8 g, 43 mmol) of a 10.0 M solution of n-butyllithium in hexane. After stirring for 30 min. at -70° C., 2.3 mL (3.3 g, 20 mmole) of benzyl bromide was added. After 18 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 the crude product. This was chromatographed on silica gel using 35%-45% ethyl acetate/hexane to yield 5.3 g of pure 3-[(4-methoxyphenyl)sulfonyl]-4-phenylbutan-1-ol, m/z=327 (M+Li).

Workup

  1. waitAfter 18 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 the crude product
  10. customThis was chromatographed on silica gel using 35%-45% ethyl acetate/hexane

Sources & evidence

ORD record
ord-af8597a428ac49cc8fe25e371876949a
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

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