3,4-dihydro-2H-pyran → HCID 19378105, compound

HRID 2211021Notes

Reaction equation

HRID 2211021 reaction equation
[CH2:1]([N:8]1[CH:12]([CH2:13][SH:14])[CH2:11][CH:10]([CH2:15][SH:16])[C:9]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1>CCOCC.C1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([N:8]1[CH:12]([CH2:13][S:14][CH:23]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[CH2:11][CH:10]([CH2:15][S:16][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][O:18]2)[C:9]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 19378148HCID 19378148, compound

Product 1

HCID 19378105HCID 19378105, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-benzyl-2,4-bis(mercaptomethyl)-4-butanelactam (compound No.15-2, 134 mg) in dry ether (2 ml), dihydropyran (110 mg) dissolved in dry ether (2 ml) is added under nitrogen atmosphere and then boron trifluoride diethyl ether complex (15 mg) dissolved in dry ether (1 ml) is added to the mixture. The mixture is stirred overnight at room temperature. The mixture is diluted with a mixture of benzene and ethyl acetate and washed with 10% aqueous sodium bicarbonate solution, water and saturated sodium chloride solution. The organic layer is dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue is purified by silica gel column chromatography to give the titled compound.

Workup

  1. additionis added under nitrogen atmosphere
  2. additionis added to the mixture
  3. washwashed with 10% aqueous sodium bicarbonate solution, water and saturated sodium chloride solution
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe oily residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6c2354e6acf4474199458f43e309548d
Source dataset
uspto-grants-1995_10
Patent number
US05461158

Reaction notes

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