6-Oxabicyclo[3.1.0]hexane → HCID 26595041, compound

HRID 418899Notes

Reaction equation

HRID 418899 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][CH:8]=1.[CH:11]12[O:16][CH:12]1[CH2:13][CH2:14][CH2:15]2>O1CCCC1.[Cu]I>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@H:11]2[CH2:15][CH2:14][CH2:13][C@H:12]2[OH:16])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 92446-Oxabicyclo[3.1.0]hexaneHCID 178490745HCID 178490745, compound

Product 1

HCID 26595041HCID 26595041, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methoxyphenyl magnesium bromide 1.0M (59.4 ml, 59.4 mmoles) and copper(I) iodide (0.762 g, 4.0 mmoles), add (dropwise) a solution of cyclopentene oxide (5.2 ml, 59.4 mmoles) in tetrahydrofuran (5 ml) over 40 minutes. The reaction is exothermic and the temperature rises to 45° C. Cool the reaction to ambient temperature and quench with a 25% solution of ammonium chloride (40 ml), extract with ether and shake with brine. Dry the organic layer over sodium sulfate and concentrate in vacuo to yield an oil which is flash chromatographed on silica with 14-25% ethyl acetate/hexanes to yield 6.43 g of the titled compound. 1H NMR (CDCl3): 7.23 (d, J=8.4, 1H), 6.86 (d, J=7.6 Hz, 1H), 6.81 (s, 1H), 6.77 (m, 1H), 4.15 (m, 1H), 3.81 (s, 3H), 2.86 (m, 1H), 2.18-2.04 (m, 2H), 1.9-1.6 (m, 5H).

Workup

  1. customrises to 45° C
  2. temperatureCool
  3. customthe reaction to ambient temperature
  4. customquench with a 25% solution of ammonium chloride (40 ml)
  5. extractionextract with ether
  6. dry with materialDry the organic layer over sodium sulfate
  7. concentrationconcentrate in vacuo
  8. customto yield an oil which
  9. customchromatographed on silica with 14-25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e1419f875da14cc4adfde3419835fac5
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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