3,6-Dioxabicyclo[3.1.0]hexane → 946125-01-5

HRID 918890Notes

Reaction equation

HRID 918890 reaction equation
[O:1]1[CH:6]2[CH:2]1[CH2:3][O:4][CH2:5]2.[C:7]1([Mg]Br)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>[Cu]I.C1COCC1>[C:7]1([C@@H:2]2[CH2:3][O:4][CH2:5][C@H:6]2[OH:1])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 675113,6-Dioxabicyclo[3.1.0]hexaneHCID 178418255HCID 178418255, compound

Product 1

HCID 14785278946125-01-5

Reagents, catalysts & solvents 2

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

Procedure

A second batch was obtained according to the above procedure reacting 3,4-epoxy-tetrahydrofuran (1.0 g, 11.62 mmol), phenylmagnesium bromide (3.872 mL, 11.62 mmol), CuI (155.67 mg, 0.813 mmol) and dry THF (total volume of 3.6 mL). The residues obtained from the above two batches was mixed and purified by flash chromatography (silica; DCM in MeOH 0/100 to 10/90). The desired fractions were collected and evaporated in vacuo to give I-42 (5.5 g, 74%) as a yellow oil.

Workup

  1. customA second batch was obtained
  2. customThe residues obtained from the above two batches
  3. additionwas mixed
  4. custompurified by flash chromatography (silica; DCM in MeOH 0/100 to 10/90)
  5. customThe desired fractions were collected
  6. customevaporated in vacuo
  7. customto give I-42 (5.5 g, 74%) as a yellow oil

Sources & evidence

ORD record
ord-21fb0cf3eef74560a22d4279e86237f9
Source dataset
uspto-grants-2016_03
Patent number
US09271967B2

Reaction notes

Loading…