Peracetic Acid → 3-((R)-5-Cyclohexyl-3-methyl-pentyl)-2,2-dimethyl-oxirane

HRID 349809Notes

Reaction equation

[CH3:1][C@@H:2]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C(=O)(O)[O-:18].[Na+].C(OO)(=O)C.S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH:5]1([CH2:4][CH2:3][C@@H:2]([CH3:1])[CH2:11][CH2:12][CH:13]2[O:18][C:14]2([CH3:15])[CH3:16])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

A flask was charged with 11.48 g (51.6 mmol) of crude (3R)-(3,7-dimethyl-oct-6-enyl)-cyclohexane, 100 mL of dichloromethane, and 9.33 g (111 mmol) of sodium bicarbonate. The mixture was cooled in a 0° C. bath. Slowly 11.6 mL (55.2 mmol) 32% peracetic acid was added. The mixture was stirred for 4 hours at 0° C. Then 10% aqueous sodium sulfite was added slowly until bubbling ceased. The layers were separated, and the organic layer was washed twice with 10% aqueous sodium sulfite and dried over magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed under reduced pressure. The remaining residue was 10.65 g (87%) of a clear oil: 1H NMR (400 MHz, CDCl3) ppm 0.86 (m, 5 H) 1.00 (d, J=6.59 Hz, 2 H) 1.14 (m, 7 H) 1.25 (s, 3 H) 1.29 (s, 3 H) 1.35 (m, 2 H) 1.50 (m, 3 H) 1.65 (m, 5 H) 2.68 (td, J=6.16, 1.83 Hz, 1 H). MS (APCl) m+1/z=239.

Workup

customuntil bubbling
customThe layers were separated
washthe organic layer was washed twice with 10% aqueous sodium sulfite
dry with materialdried over magnesium sulfate
customThe drying agent was removed by filtration
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-d8143efb73b44a87a86e44918dafc1b8
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179934B2

Reaction notes

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