Chloroform → HCID 559335, compound

HRID 1295072Notes

Reaction equation

HRID 1295072 reaction equation
[O:1]1[C:5]2([CH2:9][CH2:8][CH:7]=[CH:6]2)[O:4][CH2:3][CH2:2]1.[OH-].[Na+].[CH:12](Cl)([Cl:14])[Cl:13]>C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[Cl:13][C:12]1([Cl:14])[CH:9]2[CH:8]1[CH2:7][CH2:6][C:5]12[O:4][CH2:3][CH2:2][O:1]1

Participants

7

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 69668Cyclopent-2-en-1-one-ethyleneacetal

Product 1

HCID 559335HCID 559335, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 1,4-dioxa-spiro[4.4]non-6-ene (25.23 g, 0.20 mol) in CHCl3 (200 mL) and CH2Cl2 (200 mL) was added triethylbenzylammonium chloride (100 mg) and 50% NaOH solution (200 mL) at rt. This solution was vigorously stirred at 45° C. over 3 days. The reaction mixture was diluted with H2O (300 mL) and extracted with CHCl3 (2×150 mL). The combined organic layer was concentrated in vacuo and the residue was purified by SiO2 column chromatography (0–50% CH2Cl2 in Hexanes) to the title compounds as a colorless liquid. 1H NMR (400 MHz, CDCl3): δ 4.06–3.93 (m, 4 H), 2.25–2.01 (m, 5H), 1.89–1.83 (m, 1H).

Workup

  1. extractionextracted with CHCl3 (2×150 mL)
  2. concentrationThe combined organic layer was concentrated in vacuo
  3. customthe residue was purified by SiO2 column chromatography (0–50% CH2Cl2 in Hexanes) to the title compounds as a colorless liquid

Sources & evidence

ORD record
ord-6049a7a630094794b9af8a409b5a808e
Source dataset
uspto-grants-2007_07
Patent number
US07241792B2

Reaction notes

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