Iodoethane → HCID 14789683, compound

HRID 1090936Notes

Reaction equation

HRID 1090936 reaction equation
C(O)CCCC[OH:6].I[CH2:9][CH3:10].[H-].[Na+].[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1.[O:26]1C=CCCC1.C1(C)C([S:38]([OH:41])(=[O:40])=[O:39])=CC=CC=1.C([O:45]O)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C1COCC1.C(Cl)Cl.N1C=CC=CC=1>[OH:39][S:38]([OH:41])(=[O:45])=[O:40].[OH2:6].[C:18]([OH:26])(=[O:13])[CH2:17][CH2:16][CH2:15][CH2:14][O:19][CH2:20][CH2:25][CH2:24][CH2:23][CH2:22][O:21][CH2:9][CH3:10]

Participants

13

Reactant 8

HCID 6340IodoethaneHCID 69252-Methylbenzenesulfonic acidHCID 73974-Toluenesulfonyl chlorideHCID 80803,4-dihydro-2H-pyranHCID 81051,5-PentanediolHCID 24758Sodium hydrideHCID 62472Ethyl hydroperoxideHCID 263182Tetrahydropyranyl ether

Product 2

HCID 14789683HCID 14789683, compoundHCID 21910475Sulfuric acid hydrate (1:1)

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Commercially available 1,5-pentanediol was mono-ethylated (2, 71%) using an equivalent of iodoethane and NaH in THF. The diol was also converted into its mono-tetrahydropyranyl ether (4, 54%) by treatment with dihydropyran and toluenesulfonic acid in methylene chloride [Ngooi et al., J. Org. Chem. 54, 911 (1989 )]. Ethoxyalcohol 2 was tosylated (pyridine, TsCl, 0° C.) in 40% yield to afford oily 3. The low yield reflects the need to distill this reactive ether. Tosylate 3 was then allowed to react with mono-THP alcohol 4 (NaH, THF, reflux, 24h) to afford, after deprotection, [Corey et al., J. Am. Chem. Soc. 91, 4318 (1969), the diether alcohol, 6, in 37% yield. Oxidation using Kiliani reagent (Na2Cr2O7 --2H2O/H2SO4 /H2O) [Kiliani and Merk, Chem. Ber. 34 3562 (1901)] afforded 6,12-dioxatetradecanoic acid, 1, in 52% yield as a colorless oil.

Workup

  1. customto afford oily 3
  2. customThe low yield
  3. distillationto distill this reactive ether
  4. customto react with mono-THP alcohol 4 (NaH, THF, reflux, 24h)
  5. customto afford

Sources & evidence

ORD record
ord-be575f4e31b64bb0860ec8fa3f562596
Source dataset
uspto-grants-1992_01
Patent number
US05082967

Reaction notes

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