3,4-dihydro-2H-pyran → HCID 14823513, compound

HRID 1249246Notes

Reaction equation

HRID 1249246 reaction equation
[Cl:1][CH2:2][CH:3]([OH:14])[CH2:4][C:5]([NH:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:6].C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1.[O:32]1[CH:37]=[CH:36][CH2:35][CH2:34][CH2:33]1.C(OCC)(=O)C>C(Cl)Cl>[Cl:1][CH2:2][CH:3]([O:14][CH:33]1[CH2:34][CH2:35][CH2:36][CH2:37][O:32]1)[CH2:4][C:5]([NH:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:6]

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 8857Ethyl AcetateHCID 161440Pyridine 4-methylbenzene-1-sulfonateHCID 13813833HCID 13813833, compound

Product 1

HCID 14823513HCID 14823513, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g Ethyl 2-(4-chloro-3-hydroxybutanamido)acetate is dissolved in 10 ml CH2Cl2. 100 mg pyridine p-toluenesulphonate and 0.5 ml dihydropyran are added. The mixture is stirred for 7 h. The solvent is evaporated and the residue chromatographed, eluting with ethyl acetate. A colourless oil is obtained, Rf 0.5 (silica gel plates, thickness 0.25 mm, eluent ethyl acetate).

Workup

  1. customThe solvent is evaporated
  2. customthe residue chromatographed
  3. washeluting with ethyl acetate
  4. customA colourless oil is obtained

Sources & evidence

ORD record
ord-c10eb838a8ce4ebe995e79021f7ecfdf
Source dataset
uspto-grants-1986_12
Patent number
US04629797

Reaction notes

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