2,2-diethoxy-1-(5-(2-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl)-2-thioxo-1,3-dithiol-4-yl)ethanone → 4-(Diethoxymethyl)-4-hydroxy-6,6-dimethyl-4,6-dihydro-[1,3]dithiolo[4,5-c]furan-2-thione

HRID 389292Notes

Reaction equation

HRID 389292 reaction equation
[CH2:1]([O:3][CH:4]([O:23][CH2:24][CH3:25])[C:5]([C:7]1[S:8][C:9](=[S:22])[S:10][C:11]=1[C:12]([O:15]C1CCCCO1)([CH3:14])[CH3:13])=[O:6])[CH3:2]>C(Cl)Cl>[CH2:1]([O:3][CH:4]([O:23][CH2:24][CH3:25])[C:5]1([OH:6])[O:15][C:12]([CH3:14])([CH3:13])[C:11]2[S:10][C:9](=[S:22])[S:8][C:7]1=2)[CH3:2]

Participants

3

Reactant 1

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

Product 1

HCID 866713764-(Diethoxymethyl)-4-hydroxy-6,6-dimethyl-4,6-dihydro-[1,3]dithiolo[4,5-c]furan-2-thione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 mg (0.024 mmol) of 2,2-diethoxy-1-(5-(2-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl)-2-thioxo-1,3-dithiol-4-yl)ethanone 5 was dissolved in 5 mL of CH2Cl2 containing 0.1 mL CF3COOH. The reaction mixture was stirred for 12 hours, washed with 20 mL of saturated solution of NaHCO3 and, the organic layer was separated and dried in vacuum to yield the target compound 4 as a solid material. Yield: 7.2 mg (0.02 mmol, 90%).

Workup

  1. washwashed with 20 mL of saturated solution of NaHCO3
  2. customthe organic layer was separated
  3. customdried in vacuum

Sources & evidence

ORD record
ord-6673f3f81b574d249eb60b8da275461d
Source dataset
uspto-grants-2013_02
Patent number
US08378123B2

Reaction notes

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