4-Phenyl-1,3-dithiolane-2-thione → 2,2-diethoxy-1-(5-(2-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl)-2-thioxo-1,3-dithiol-4-yl)ethanone

HRID 389291Notes

Reaction equation

HRID 389291 reaction equation
[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[C:5](=[O:18])[C:6]#[C:7][C:8]([CH3:17])([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH3:9])[CH3:2].C1(C2C[S:31][C:30](=[S:33])[S:29]2)C=CC=CC=1>ClCCl>[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[C:5]([C:6]1[S:31][C:30](=[S:29])[S:33][C:7]=1[C:8]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)([CH3:17])[CH3:9])=[O:18])[CH3:2]

Participants

4

Reactant 2

HCID 2639824-Phenyl-1,3-dithiolane-2-thioneHCID 683253631,1-diethoxy-5-methyl-5-(tetrahydro-2H-pyran-2-yloxy)hex-3-yn-2-one

Product 1

HCID 866713752,2-diethoxy-1-(5-(2-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl)-2-thioxo-1,3-dithiol-4-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 1,1-diethoxy-5-methyl-5-(tetrahydro-2H-pyran-2-yloxy)hex-3-yn-2-one 3 (1.5 g, 5.0 mmol) and 4-phenyl-1,3-dithiolane-thione (5.3 g, 25.0 mmol) was heated under N2 at 130° C. for 1 hour. The reaction was monitored by thin layer chromatography using silica gel as the stationary phase and dichloromethane as the mobile phase. The color of the reaction mixture changed from yellow to dark orange. After completion of the reaction, as evidenced by TLC, the reaction was stopped, cooled, and the target compound 4 was purified by radial chromatography using silica gel as the stationary phase. The target compound 4 eluted as the third fraction with a mixture of dichloromethane and hexanes (60:40). The first band was the excess 4-phenyl-1,3-dithiolane-thione, and the second band yielded 2,2-diethoxy-1-(5-(2-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl)-2-thioxo-1,3-dithiol-4-yl)ethanone 5 which was further converted to 4-(diethoxymethyl)-4-hydroxy-6,6-dimethyl-4,6-dihydro-[1,3]dithiolo[4,5-c]furan-2-thione 4.

Workup

  1. customAfter completion of the reaction
  2. temperaturecooled
  3. customthe target compound 4 was purified by radial chromatography
  4. washThe target compound 4 eluted as the third fraction with a mixture of dichloromethane and hexanes (60:40)

Sources & evidence

ORD record
ord-a16f83b52e1b47d7bd07dd92948f9e04
Source dataset
uspto-grants-2013_02
Patent number
US08378123B2

Reaction notes

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