Hydrogen Peroxide → HCID 86703721, compound

HRID 1849833Notes

Reaction equation

HRID 1849833 reaction equation
C1([Se][C:8]2([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)C=CC=CC=1.OO>ClCCl>[O:12]1[C:11]2([CH2:16][CH2:17][C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:9][CH2:10]2)[O:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 86703720Ethyl 8-(phenylselanyl)-1,4-dioxaspiro[4.5]decane-8-carboxylate

Product 1

HCID 86703721HCID 86703721, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 8-(phenylselanyl)-1,4-dioxaspiro[4.5]decane-8-carboxylate (14.00 g, 38.00 mmol) in dichloromethane (100 mL) was added 30% hydrogen peroxide solution (11.6 mL, 380.0 mmol). The reaction mixture was stirred at ambient temperature for 16 h then diluted with dichloromethane (100 mL), washed with saturated sodium hydrogencarbonate (100 mL), saturated ammonium chloride (3×75 mL), and brine (3×75 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was purified by column chromatography with ethyl acetate in hexanes (10%) to afford the title compound as a colorless liquid (6.10 g, 76%): 1H NMR (300 MHz, CDCl3) δ 6.82 (m, 1H), 4.11 (dd, J=7.1 Hz, 2H), 3.92 (s, 4H), 2.49-2.43 (m, 2H), 2.34-2.29 (m, 2H), 1.76-1.65 (m, 4H), 1.21 (t, J=7.1 Hz, 3H).

Workup

  1. washwashed with saturated sodium hydrogencarbonate (100 mL), saturated ammonium chloride (3×75 mL), and brine (3×75 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo to dryness
  5. customThe residue was purified by column chromatography with ethyl acetate in hexanes (10%)

Sources & evidence

ORD record
ord-caf47b30310f45b4b8128d06996f6850
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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