Triphenylphosphine → 5-(5-Chloro-2,3-dihydrobenzofuran-7-yl)-3-(1-butylpiperidin-4-yl)-1,3,4-oxadiazol-2(3H)-one

HRID 583130Notes

Reaction equation

HRID 583130 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[O:15][C:14](=[O:16])[NH:13][N:12]=2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[CH2:17]([N:21]1[CH2:26][CH2:25][CH:24](O)[CH2:23][CH2:22]1)[CH2:18][CH2:19][CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC([O-])=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[O:15][C:14](=[O:16])[N:13]([CH:24]3[CH2:25][CH2:26][N:21]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:22][CH2:23]3)[N:12]=2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 136652701-Butylpiperidin-4-olHCID 211877245-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,3,4-oxadiazol-2(3H)-oneHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 213106155-(5-Chloro-2,3-dihydrobenzofuran-7-yl)-3-(1-butylpiperidin-4-yl)-1,3,4-oxadiazol-2(3H)-oneYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2.38 g (0.01 mol) of 5-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,3,4-oxadiazol-2(3H)-one, in suspension in 80 ml of tetrahydrofuran, are introduced into a 250 ml three-necked round-bottomed flask, cooled to 0° C. and placed under magnetic stirring, 1.57 g (0.01 mol) of 1-butylpiperidin-4-ol, 3.41 g (0.013 mol) of triphenylphosphine and then 2.44 g (0.014 mol) of ethyl azodicarboxylate are added and the mixture is stirred at room temperature for 3 h and then at 40° C. for 3 h. The solvent is evaporated under reduced pressure and the residue is taken up in water and extracted five times with diethyl ether. The organic phase is dried over magnesium sulphate and filtered, the solvent is evaporated under reduced pressure and the residue is purified by chromatography on a column of silica gel, elution being carried out with an 80/20 mixture of ethyl acetate and heptane. 3 g of compound are obtained. Melting point: 133.8-134° C.

Workup

  1. waitat 40° C. for 3 h
  2. customThe solvent is evaporated under reduced pressure
  3. extractionextracted five times with diethyl ether
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent is evaporated under reduced pressure
  7. customthe residue is purified by chromatography on a column of silica gel, elution
  8. additionbeing carried out with an 80/20 mixture of ethyl acetate and heptane

Sources & evidence

ORD record
ord-3c6d65742bde44c29fc788d45208a8ad
Source dataset
uspto-grants-1999_07
Patent number
US05929089

Reaction notes

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