Hexane → HCID 19811009, compound

HRID 373717Notes

Reaction equation

HRID 373717 reaction equation
C([Li])CCC.[NH:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11].[C:12]1([S:18](C2CC(Cl)CC2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>O1CCCC1>[CH2:28]1[CH2:29][CH:30]([C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:18]([N:6]2[CH2:10][CH2:9][CH2:8][C:7]2=[O:11])(=[O:19])=[O:20])[CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 120252-PyrrolidoneHCID 54568464HCID 54568464, compoundHCID 178418339Butyllithium

Product 1

HCID 19811009HCID 19811009, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8 cm3 of a 1.5M solution of n-butyllithium in n-hexane is poured into a solution comprising 1.02 g, or 0.9 cm3, of 2-pyrrolidinone in 50 cm3 of tetrahydrofuran, cooled to -70° C., without the temperature exceeding -60° C. After 15 minutes, 3 g of benzenesulphonyl-4-cyclopentyl chloride in solution in 12 cm3 of tetrahydrofuran is added, maintaining the temperature between -65° and -70° C. After allowing to return to ambient temperature over 2 hours and evaporating to dryness, the residue is chromatographed on silica (eluent: ethyl acetate-n-hexane 1-3) and 2.6 g of expected product is obtained.

Workup

  1. customexceeding -60° C
  2. temperaturemaintaining the temperature between -65° and -70° C
  3. waitto return to ambient temperature over 2 hours
  4. customevaporating to dryness
  5. customthe residue is chromatographed on silica (eluent: ethyl acetate-n-hexane 1-3)

Sources & evidence

ORD record
ord-77bfe87e2af942a0a407bccd85409c1a
Source dataset
uspto-grants-1992_11
Patent number
US05164514

Reaction notes

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