Dimethyl Sulfoxide → Methyl 8-methylsulfonyl-12-acetoxy-13-(3-trifluoromethylphenoxy)tridecanoate

HRID 1833488Notes

Reaction equation

[CH3:1][S:2]([C:5](C(OC)=O)([CH2:16][CH2:17][CH2:18][CH:19]([O:32][C:33](=[O:35])[CH3:34])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:4])=[O:3].[Cl-].[Na+].CS(C)=O>O>[CH3:1][S:2]([CH:5]([CH2:16][CH2:17][CH2:18][CH:19]([O:32][C:33](=[O:35])[CH3:34])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:29])[F:30])[CH:23]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:3])=[O:4]

Participants

Conditions

Temperature: 185 °C

Procedure

A mixture of methyl 8-methylsulfonyl-8-methoxycarbonyl-12-acetoxy-13-(3-trifluoromethylphenoxy)tridecanoate (5.82 g., 0.01 mole), sodium chloride (0.59 g., 0.01 mole), dimethylsulfoxide (8 ml.), and water (0.2 ml.) is heated in an oil bath at 185° C. for 10 hours under nitrogen. The reaction mixture is then concentrated in vacuo on a steam bath. The dark-colored residue is diluted with water, acidified with 6N hydrochloric acid, and extracted with ether. The ether extracts are washed with water, dried with anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (9.90 g., 0.019 mole, 94%).

Workup

concentrationThe reaction mixture is then concentrated in vacuo on a steam bath
additionThe dark-colored residue is diluted with water
extractionextracted with ether
washThe ether extracts are washed with water
dry with materialdried with anhydrous magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-bca40c15d85f4690819d9c506c67a160
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04066675

Reaction notes

Loading…