Magnesium perchlorate → HCID 178472492, compound

HRID 237328

Reaction equation

[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O>ClCCl>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:6]([CH3:11])([CH3:7])[CH3:4])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@@H:9]([O:12][C:6]([CH3:11])([CH3:7])[CH3:4])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of cis/trans-4-hydroxycyclohexane carboxylic acid ethyl ester (2:1) (1.0 g, 5.8 mmol) and di-tort-butyl dicarbonate (2.9 g, 13.4 mmol) in dichloromethane (6 ml) was added anhydrous magnesium perchlorate (0.13 g, 0.58 mmol) which was previously activated in high vacuo (ca. 1 mbar) at 150° C. for 1 h. Stirring for 16 h at 40° C. was followed by partitioning between dichloromethane (50 ml) and water (30 ml). The layers were separated. The aqueous layer was extracted with one 50-ml portion of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash-chromatography with n-heptane/tert-butyl methyl ether as eluent gave pure trans-4-tert-butoxy-cyclohexanecarboxylic acid ethyl ester and cis-4-tert-butoxy-cyclohexanecarboxylic acid ethyl ester.

Workup

customby partitioning between dichloromethane (50 ml) and water (30 ml)
customThe layers were separated
extractionThe aqueous layer was extracted with one 50-ml portion of dichloromethane
dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customPurification by flash-chromatography with n-heptane/tert-butyl methyl ether as eluent

Sources & evidence

ORD record: ord-ff3942f6ef564a28963eefe7a0353ea6
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642590B2

Linked notes

Loading…