Hydrogen Peroxide → HCID 67975667, compound

HRID 1844079Notes

Reaction equation

HRID 1844079 reaction equation
[CH2:1]1[CH:4]2[CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH:3]2[C:2]1=[O:12].[OH:13]O.[Na]>C(O)(=O)C.O>[O:13]1[C:2](=[O:12])[CH2:1][CH:4]2[CH2:5][CH:6]3[C:11]([CH:10]=[CH:9][CH:8]=[CH:7]3)=[C:3]12

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 4356718202264-45-7HCID 5360545Sodium

Product 1

HCID 67975667HCID 67975667, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1,2a,7,7a-tetrahydro-2H-Cyclobut[a]inden-2-one (Example I4, 0.377 mg, 2.383 mmol) in acetic acid (5 mL) and water (0.5 mL) was cooled at 0° C. and hydrogen peroxide (30% in water, 0.810 mL, 7.14 mmol) was added. The solution as stirred for 3 h at 0° C. and the reaction mixture was poured into saturated solution of sodium hydrogenocarbonate. The solution was extracted with ethyl acetate and the combined organic layers were washed with brine, dried and concentrated. The residue was purified by flash chromatography eluting with cyclohexane and ethyl acetate (4/1) to give rac-Tetrahydroindeno[1,2-b]furan-2-one (Colourless oil, 383 mg, 92%), that solidified upon cooling (data match with litt data, CAS 4471-33-4). C11H10O2; MW: 174.20; LCMS (method A) RT 1.32 min; ES: 175 (60%, MH+), 129 (100%); IR: 1769 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.50 (1H, d), 7.25-7.39 (4H, m), 5.91 (1H, d), 3.28-3.45 (2H, m), 2.86-2.97 (2H, m), 2.41 (1H, dd) ppm.

Workup

  1. customwas cooled at 0° C.
  2. extractionThe solution was extracted with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with cyclohexane and ethyl acetate (4/1)

Sources & evidence

ORD record
ord-522ee45bfb58420ebea0a0dc89ff1934
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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