Triphenylphosphine → 4-[4-(p-Chlorophenylsulfonamido)butyl)-epsilon-caprolactone

HRID 1494098Notes

Reaction equation

HRID 1494098 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH2:13][CH2:12][O:11][C:9](=[O:10])[CH2:8][CH2:7]1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl.O1CCCC1>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([S:21]([NH:24][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]2[CH2:13][CH2:12][O:11][C:9](=[O:10])[CH2:8][CH2:7]2)(=[O:22])=[O:23])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 668244-ChlorobenzenesulfonamideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 103300695-(4-Hydroxybutyl)oxepan-2-one

Product 1

HCID 103611324-[4-(p-Chlorophenylsulfonamido)butyl)-epsilon-caprolactone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.53 g of 4-(4-hydroxybutyl)-epsilon-caprolactone in 14 mL methylene chloride and 14 mL tetrahydrofuran is added 4.24 g p-chlorophenylsulfonamide followed by 7.44 g triphenylphosphine. The reaction mixture is stirred at room temperature for one half hour and then 6.1 mL diethyl azodicarboxylate is added slowly with cooling. After the addition, the cooling bath is removed and the solution is stirred at room temperature overnight. The reaction mixture is evaporated to dryness to yield 4-[4-(p-chlorophenylsulfonamido)butyl]-epsilon-caprolactone.

Workup

  1. temperaturewith cooling
  2. additionAfter the addition
  3. customthe cooling bath is removed
  4. stirringthe solution is stirred at room temperature overnight
  5. customThe reaction mixture is evaporated to dryness

Sources & evidence

ORD record
ord-a148ff74f1554a369f161a66253d700b
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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