Methanol → HCID 70099319, compound

HRID 1385299Notes

Reaction equation

HRID 1385299 reaction equation
[H-].[Na+].[CH:3](OCC)=[O:4].[C:8]([C:11]1[S:12][C:13]([S:23][CH3:24])=[C:14]2[C:19](=[O:20])[CH2:18][C:17]([CH3:22])([CH3:21])[CH2:16][C:15]=12)(=[O:10])[CH3:9].CO>C1COCC1.O>[CH3:22][C:17]1([CH3:21])[CH2:16][C:15]2=[C:11]([C:8](=[O:10])[CH:9]=[CH:3][OH:4])[S:12][C:13]([S:23][CH3:24])=[C:14]2[C:19](=[O:20])[CH2:18]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 27787521-Acetyl-6,6-dimethyl-3-(methylsulfanyl)-6,7-dihydro-2-benzothiophen-4(5H)-one

Product 1

HCID 70099319HCID 70099319, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (149 mg of a 60% dispersion in oil. 3.7 mmol) in THF (7 mL) was added ethyl formate (0.75 mL, 9.3 mmol) at 0° C., under nitrogen. After addition a solution of 1-acetyl-6,6-dimethyl-3-methylthio-4,5,6,7-tetrahydrobenzo [c]thiophen-4-one (0.5 g, 1.9 mmol) in THF (7 mL) was added. The mixture was stirred overnight at room temperature. Methanol (0.5 mL) and water (0.5 mL) were then added to the mixture and the solvent removed in vacuo. The residue was dissolved in water and acidified using 1M HCl. The resultant solid was collected by filtration then partitioned between EtOAc (30 mL) and water (30 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was triturated with ether and the title compound (0.4 g, 80%) was isolated as a yellow solid. 1H NMR (360 MHz, CDCl3) δ 1.09 (6H, s), 2.43 (2H, s), 2.63 (3H, s), 3.08 (2H, s), 5.85 (1H, d, J=5.1 Hz), 7.77 (1H, d, J=5.1 Hz), 14.90 (1H, br s). MS (ES+) 297 (M+1).

Workup

  1. additionwas added
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. filtrationThe resultant solid was collected by filtration
  5. customthen partitioned between EtOAc (30 mL) and water (30 mL)
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-eda370a4f3fd48529ffd75174b1178d9
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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