Triacetoxyperiodinane → HCID 178447962, compound

HRID 2039377Notes

Reaction equation

[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7](/[CH:10]=[CH:11]/[CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:1]([C@H:4]1[CH2:5][CH2:6][C@H:7](/[CH:10]=[CH:11]/[CH2:12][CH2:13][CH:14]2[CH2:15][CH2:16][C:17](=[O:20])[CH2:18][CH2:19]2)[CH2:8][CH2:9]1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

(E)-4-(4-(trans-4-Propylcyclohexyl)but-3-en-1-yl)cyclohexanol (s44) (4.7 g) and methylene chloride (100 ml) were placed in a reaction vessel under an atmosphere of nitrogen, and cooled to 0° C. Dess-Martin periodinane (DMP; 9.3 g) was added in the temperature range of 0° C. to 5° C. After 1 hour of stirring at 0° C., the reaction mixture was allowed to come to room temperature, and the stirring was continued for another 8 hours. Celite was added to the reaction mixture, and unnecessary materials were removed. The solution was concentrated under reduced pressure, and the residue was purified by column chromatography with toluene as an eluent and silica gel as a stationary phase powder to give (E)-4-(4-(trans-4-propylcyclohexyl)but-3-en-1-yl)cyclohexanone (s45) (4.6 g). The yield based on the compound (s44) was 98.6%.

Workup

customto come to room temperature
waitthe stirring was continued for another 8 hours
additionCelite was added to the reaction mixture, and unnecessary materials
customwere removed
concentrationThe solution was concentrated under reduced pressure
customthe residue was purified by column chromatography with toluene as an eluent

Sources & evidence

ORD record: ord-e63d91a3062e49e3be2f42563acc8c9b
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580146B2

Reaction notes

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