3,4-dihydro-2H-pyran → HCID 21284017, compound

HRID 1249243Notes

Reaction equation

HRID 1249243 reaction equation
[Br: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.[NH+]1C=CC=CC=1.[O:32]1[CH:37]=[CH:36][CH2:35][CH2:34][CH2:33]1.C(OCC)(=O)C>C(Cl)Cl>[Br: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 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21284022Ethyl 2-(4-bromo-3-hydroxybutanamido)acetate

Product 1

HCID 21284017HCID 21284017, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1 g ethyl 2-(4-bromo-3-hydroxybutanamido)acetate in 30 ml methylene chloride are added 100 mg pyridinium p-toluenesulphonate and 1 ml dihydropyran. Stirring is continued for 3 h at ambient temperature, the solvent is evaporated in vacuo and the residue chromatographed on silica, eluting with ether. A pale straw-coloured oil is obtained in 91% yield, Rf 0.5 (silica gel plates, thickness 0.25 mm eluent ethyl acetate).

Workup

  1. customthe solvent is evaporated in vacuo
  2. customthe residue chromatographed on silica
  3. washeluting with ether
  4. customA pale straw-coloured oil is obtained in 91% yield, Rf 0.5 (silica gel plates

Sources & evidence

ORD record
ord-543c15138b7c4ccabaae404ceabc20ea
Source dataset
uspto-grants-1986_12
Patent number
US04629797

Reaction notes

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