tert-Butanol → methyl 2-methyl-6-[(1R,3S)-3-(2-oxoethoxy)cyclohexyloxymethyl]benzoate

HRID 1353166Notes

Reaction equation

[CH2:1]([O:4][C@H:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([O:11][CH2:12][C:13]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:14]=2[C:15]([O:17][CH3:18])=[O:16])[CH2:6]1)[CH:2]=C.I([O-])(=O)(=O)=[O:25].[Na+].C(O)(C)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)C.O.[Os](=O)(=O)(=O)=O>[CH3:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:13]([CH2:12][O:11][C@@H:7]2[CH2:8][CH2:9][CH2:10][C@H:5]([O:4][CH2:1][CH:2]=[O:25])[CH2:6]2)[C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

Conditions

Temperature: 0 °C

Procedure

1.0 g of methyl 2-((1R,3S)-3-allyloxycyclohexyloxymethyl)-6-methylbenzoate is dissolved in 30 ml of diethyl ether, and 2.0 g of sodium periodate, dissolved in 30 ml of water, are added. At 0° C., 2 ml of a solution of 2.5% by weight of osmium tetroxide and tert-butanol are added. The reaction mixture is stirred vigorously for three hours. The mixture is then cooled to 0° C., and 50 ml of a saturated sodium thiosulfate solution are added. The organic phase is removed. The aqueous phase is extracted three times with in each case 20 ml of diethyl ether. The combined organic phases are dried over magnesium sulfate and the solvent is then removed under reduced pressure. This gives 1.0 g of methyl 2-methyl-6-[(1R,3S)-3-(2-oxoethoxy)cyclohexyloxymethyl]benzoate as a yellow oil C18H24O5 (320.39), MS(ESI): 321 (M+H+), Rf=0 23 (n-heptane:ethyl acetate=1:1).

Workup

additionare added
customThe organic phase is removed
extractionThe aqueous phase is extracted three times with in each case 20 ml of diethyl ether
dry with materialThe combined organic phases are dried over magnesium sulfate
customthe solvent is then removed under reduced pressure

Sources & evidence

ORD record: ord-6b8544f26c8940a39d3e21cdba91d550
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220876B2

Reaction notes

Loading…