Dimethylformamide → HCID 67873983, compound

HRID 867986Notes

Reaction equation

[C:1]([C:9]1[CH:18]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[C:12]([OH:19])=[CH:11][CH:10]=1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2].Cl[CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1.C(=O)([O-])[O-:37].[K+].[K+].CN(C)C=O>CCOCC>[O:31]1[CH2:32][CH2:33][CH2:34][CH2:35][CH:30]1[O:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:19][C:12]1([OH:37])[CH:11]=[CH:10][C:9]([C:1]([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:2])[CH3:3])=[CH:18][CH:13]1[C:14]([O:16][CH3:17])=[O:15]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of methyl 5-t-octylsalicylate (37.7 g, 0.143 mole), 2-(2-[2-(2-chloroethoxy)ethoxy]ethoxy)tetrahydropyran (54 g, 0.214 mole), potassium carbonate (28 g, 0.217 mole) and N,N-dimethylformamide (250 ml) was heated at 140° C., under nitrogen, for 18 hours, with stirring. The mixture was cooled, diluted with ether, and then washed liberally with saturated sodium chloride solution. The ethereal solution was dried (MgSO4) and evaporated in vacuo to give an oil, which was chromatographed on silica gel to give 46 g of methyl 2-(2-[2-(2-[2-tetrahydropyranyloxy]ethoxy)ethoxy]ethoxy)-5-t-octylsalicylate.

Workup

temperatureThe mixture was cooled
washwashed liberally with saturated sodium chloride solution
dry with materialThe ethereal solution was dried (MgSO4)
customevaporated in vacuo
customto give an oil, which
customwas chromatographed on silica gel

Sources & evidence

ORD record: ord-a997f710c0e44781a87f096ea4431db6
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04777270

Reaction notes

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