Tetrahydrofuran → HCID 58174493, compound

HRID 1811355Notes

Reaction equation

HRID 1811355 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2Br)=[CH:3][CH:2]=1.[CH2:16]([Li])[CH2:17][CH2:18]C.C(O[N:29]1[CH2:34][CH2:33][C:32](=[O:35])[CH2:31][CH2:30]1)C1C=CC=CC=1.[O:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>>[C:40]([N:29]1[CH2:34][CH2:33][C:32]([OH:35])([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][C:4]2[CH:5]=[CH:6][C:1]([CH3:15])=[CH:2][CH:3]=2)[CH2:31][CH2:30]1)(=[O:36])[C:39]1[CH:18]=[CH:17][CH:16]=[CH:37][CH:38]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 21864904(2-Bromophenyl)(p-tolyl)sulfaneHCID 685189401-Benzyloxy-piperidin-4-oneHCID 178418339Butyllithium

Product 1

HCID 58174493HCID 58174493, compound

Conditions

Temperature
-15 °C

Procedure

2-(4-tolylsulfanyl)-phenyl bromide (6.98 g, 25 mmol) was dissolved in heptanes (40 mL) and dry tetrahydrofuran (4.1 mL) and after 1.5 hrs the reaction mixture was cooled down to 0° C. under an atmosphere of nitrogen. n-Butyl lithium in heptanes 2.7 M (9.8 mL, 26.5 mmol) was added at 0° C. and after 45 minutes the reaction mixture was cooled to −15° C. A solution of N-benzyloxy-4-piperidone (5.08 g, 25 mmol) in dry tetrahydrofuran (40 mL) was added to the reaction mixture maintaining the temperature below −15° C. Once the addition was complete the reaction was allowed to warm to room temperature before quenching with dilute aqueous HCl solution. HPLC indicated the presence of 1-methyl-4-phenylsulfanyl-benzene and a complex mixture of unknown compounds.

Workup

  1. temperaturemaintaining the temperature below −15° C
  2. additionOnce the addition
  3. temperatureto warm to room temperature
  4. custombefore quenching with dilute aqueous HCl solution
  5. additiona complex mixture of unknown compounds

Sources & evidence

ORD record
ord-4e9cdf6e129e4ec19bad40f6c5806509
Source dataset
uspto-grants-2013_01
Patent number
US08362255B2

Reaction notes

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