Dimethylformamide → HCID 70389267, compound

HRID 2352406Notes

Reaction equation

HRID 2352406 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])(C)C)(C)C.ClC[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-].[K+].[K+].CN(C)[CH:44]=[O:45]>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][CH2:44][O:45][C:12]1([OH:19])[CH:11]=[CH:10][C:9]([CH2:1][CH2:4][CH2:5][CH2:8][CH2:9][CH2:1][CH2:4][CH3:5])=[CH:18][CH:13]1[C:14]([O:16][CH3:17])=[O:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 134165072-{2-[2-(2-Chloroethoxy)ethoxy]ethoxy}oxaneHCID 15117887HCID 15117887, compound

Product 1

HCID 70389267HCID 70389267, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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, 0.124 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-octylsalicylate

Workup

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

Sources & evidence

ORD record
ord-9781b3f3da0c4d5280c06e71c665a5ac
Source dataset
uspto-grants-1989_10
Patent number
US04876367

Reaction notes

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