Water → HCID 11788660, compound

HRID 1436331Notes

Reaction equation

[CH:1]([O:3][C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:5]1[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH2:2].O>CO>[CH:1]([O:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH2:2]

Participants

Conditions

Temperature: 20 °C

Procedure

1.09 g (6.00 mmol) of cis-2-tert-butylcyclohexyl vinyl ether and 199 mg (0.30 mmol) of Co(OAc) (L3) were dissolved in 6.0 ml of methanol under the atmosphere and 540 μL (30 mmol) of water was added to the mixture and the mixture was then stirred at 20° C. After 11 hours, the reaction solution was analyzed by GC, to find that 23% of the cis-2-tert-butylcyclohexyl vinyl ether was left with an optical purity of 92% ee and comprised (1R, 2R) isomers. Further, the reaction solution was purified by silica gel column chromatography to isolate the reaction substrate 2-tert-butylcyclohexyl vinyl ether and the reaction product 2-tert-butylcyclohexanol in a ratio of 22% and 77% respectively. Also, the kre1 value showing the selectivity of reactions at this time was 4.9.

Workup

additionwas added to the mixture
waitwas left with an optical purity of 92% ee
customFurther, the reaction solution was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-ad0a1aa4a6a54e818af337db3b7daa53
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07619003B2

Reaction notes

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