Hexane → HCID 19000627, compound

HRID 2260392Notes

Reaction equation

HRID 2260392 reaction equation
[CH3:1][S:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[N:4][CH3:5])=[O:3].C1(C(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([Li])CCC.CCCCCC.[C:42]1([C:47]([CH2:49][S:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:48])[CH2:46][CH2:45][CH2:44][CH:43]=1.[Cl-].[NH4+]>C1COCC1>[C:51]1([S:50][CH2:49][C:47]([OH:48])([C:42]2[CH2:46][CH2:45][CH2:44][CH:43]=2)[CH2:1][S:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)(=[N:4][CH3:5])=[O:3])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

8

Reactant 6

HCID 8058HexaneHCID 10614TriphenylmethaneHCID 25517Ammonium ChlorideHCID 519772HCID 519772, compoundHCID 19000674HCID 19000674, compoundHCID 178418339Butyllithium

Product 1

HCID 19000627HCID 19000627, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of S-methyl-N-methyl-S-phenyl-sulfoximine (2.04 g, 12 mmol) and triphenylmethane (5 mg) in dry THF (20mL) is added dropwise to a solution of n-butyllithium (1.6 mol) in hexane (7.5 mL, 12 mmol) at 0° C. A solution of phenylthio-methyl cyclopent-1-enyl ketone (2.18 g, 10mmol) in dry THF (10 mL) is then added slowly during a period of 10 minutes. After stirring at 0° C. for 30 minutes, the mixture is poured into a 5% ammonium chloride aqueous solution (50 mL) and extracted with dichloromethane (40 mL×3). The combined extracts are washed with H2O, dried (Na2SO4), and evaporated in vacuo to dryness. The thin layer chromatography (TLC, SiO2, toluene/EtOAc, 9:1 v/v) of the mixture showed that it contains a mixture of diastereomers in a syrup, 2.70 g (70%) (Rf=0.43 and 0.37), which are isolated by liquid chromatography (SiO2, touene/EtOAc, 9:1 v/v) and used directly in the next step without further separation.

Workup

  1. extractionextracted with dichloromethane (40 mL×3)
  2. washThe combined extracts are washed with H2O
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo to dryness
  5. additiona mixture of diastereomers in a syrup, 2.70 g (70%) (Rf=0.43 and 0.37), which
  6. customare isolated by liquid chromatography (SiO2, touene/EtOAc, 9:1 v/v)
  7. customused directly in the next step without further separation

Sources & evidence

ORD record
ord-1bf8e614c6104cad999f8431a8d5dbc1
Source dataset
uspto-grants-1995_12
Patent number
US05476952

Reaction notes

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