m-Chloroperbenzoic acid → HCID 86692649, compound

HRID 1470833Notes

Reaction equation

HRID 1470833 reaction equation
[F:1][C:2]1[C:3]2[CH2:20][S:19][CH2:18][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH2:10][CH:11]([CH2:16][CH3:17])[CH2:12][CH2:13][CH2:14][CH3:15])=[O:8].C1C=C(Cl)C=C(C(OO)=O)C=1>C(OCC)(=O)C>[F:1][C:2]1[C:3]2[C:4](=[CH:18][S:19][CH:20]=2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH:11]([CH2:16][CH3:17])[CH2:12][CH2:13][CH2:14][CH3:15])=[O:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86692650HCID 86692650, compound

Product 1

HCID 86692649HCID 86692649, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
-78 °C

Procedure

475 mg of 2-ethylhexyl 3-fluoro-4,6-dihydrothieno[3,4-b]thiophene-2-carboxylate (1.50 mmol) was dissolved in 10 ml of ethyl acetate, the solution was cooled to −78° C. 337 mg of 77% m-CPBA (1.50 mmol) in 3 ml ethyl acetate was added and the reaction mixture was allowed to warm up to room temperature overnight. The solvent was removed by rotary evaporation and the residue was re-dissolved in 10 ml acetic anhydride, and heated to reflux for about 30 min. The solvent was removed by rotary evaporation and the product was purified by column (silica gel, hexane:dichloromethane=4:1) to produce 361 mg of product. The yield was about 76.5% for the two steps.

Workup

  1. temperatureto warm up to room temperature overnight
  2. customThe solvent was removed by rotary evaporation
  3. dissolutionthe residue was re-dissolved in 10 ml acetic anhydride
  4. temperatureheated
  5. temperatureto reflux for about 30 min
  6. customThe solvent was removed by rotary evaporation
  7. customthe product was purified by column (silica gel, hexane:dichloromethane=4:1)

Sources & evidence

ORD record
ord-91c794f3215f4f49ab85c3583f988acc
Source dataset
uspto-grants-2015_04
Patent number
US09006568B2

Reaction notes

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