m-Chloroperbenzoic acid → 8-(Oxiran-2-yl)-1,4-dioxaspiro[4.5]decane

HRID 2175513Notes

Reaction equation

HRID 2175513 reaction equation
[CH:1]([CH:3]1[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1)=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[O:21]1[CH2:2][CH:1]1[CH:3]1[CH2:12][CH2:11][C:6]2([O:7][CH2:8][CH2:9][O:10]2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 575989198-Vinyl-1,4-dioxaspiro[4,5]decane

Product 1

HCID 585624888-(Oxiran-2-yl)-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 8-vinyl-1,4-dioxaspiro[4.5]decane (370 mg, 2.20 mmol), prepared as described in Example 9 Step A, in DCM (20 mL) cooled to 0° C. was added mCPBA (532 mg, 2.37 mmol, 77%). The mixture was stirred warming to room temperature over 1 hour and then concentrated in vacuo without heating. The residue was purified by flash chromatography (silica gel, 0-50% ether/DCM) to afford the product.

Workup

  1. temperaturewarming to room temperature over 1 hour
  2. concentrationconcentrated in vacuo
  3. temperaturewithout heating
  4. customThe residue was purified by flash chromatography (silica gel, 0-50% ether/DCM)
  5. customto afford the product

Sources & evidence

ORD record
ord-7968900522e940c291fd149c9c350930
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

Loading…