3,4-dihydro-2H-pyran → HCID 21284014, compound

HRID 1249242Notes

Reaction equation

HRID 1249242 reaction equation
[Br:1][CH2:2][CH:3]([OH:13])[CH2:4][C:5]([NH:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:6].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:31]1[CH:36]=[CH:35][CH2:34][CH2:33][CH2:32]1>C(Cl)Cl>[Br:1][CH2:2][CH:3]([O:13][CH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][O:31]1)[CH2:4][C:5]([NH:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:6]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21284013HCID 21284013, compound

Product 1

HCID 21284014HCID 21284014, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 300 mg methyl 2-(4-bromo-3-hydroxybutanamido)acetate in 50 ml methylene chloride are added 30 mg pyridinium p-toluenesulphonate and 1 ml dihydropyran. After stirring at ambient temperature for 20 h, the solvent is evaporated in vacuo and the residue chromatographed on silica, eluting with ether. A colourless oil is obtained in 92% yield, Rf 0.33 (silica gel plates, thickness 0.25, eluent diethyl ether).

Workup

  1. customthe solvent is evaporated in vacuo
  2. customthe residue chromatographed on silica
  3. washeluting with ether
  4. customA colourless oil is obtained in 92% yield, Rf 0.33 (silica gel plates, thickness 0.25, eluent diethyl ether)

Sources & evidence

ORD record
ord-927a6b985c124583a056f8ae030c3170
Source dataset
uspto-grants-1986_12
Patent number
US04629797

Reaction notes

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