Water → HCID 20386919, compound

HRID 866368Notes

Reaction equation

HRID 866368 reaction equation
S1CCS[CH:2]1[CH2:6][CH2:7][CH:8]1[CH:19](/[CH:20]=[CH:21]/[CH:22]([OH:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:18][CH2:17][C:9]21[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2.[O:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]1OC1CCCCO1.CI.C([O-])([O-])=[O:45].[Ca+2].O>CN(C=O)C.CC(C)=O>[CH3:15][C:12]1([CH3:16])[CH2:11][O:10][C:9]2([CH2:17][CH2:18][CH:19](/[CH:20]=[CH:21]/[CH:22]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[O:28][CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][O:29]3)[CH:8]2[CH2:7][CH2:6][CH:2]=[O:45])[O:14][CH2:13]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10112Calcium CarbonateHCID 86735829HCID 86735829, compound

Product 1

HCID 20386919HCID 20386919, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

1.05 g (2.05 mmoles of 1-[7-[(1,3-dithia-2-cyclopentyl)ethyl]3,3-dimethyl-1,5-dioxaspiro[5,4]-dec-8-yl]-trans-1-octene-3-ol-tetrahydropyranyl ether was stirred for 2 hours at 50° C in 100 ml of DMF with 0.7 ml (10.3 mmoles) of methyl iodide, 1.4 g (14 moles) of CaCO3 and 0.4 ml of H2O. The solution was cooled, combined with 50 ml of acetone, filtered with suction to remove the precipitate and the filtrate was evaporated to dryness at 0.1 mm Hg. The residue was dissolved in ether, washed with H2O, dried over MgSO4 and the solvent was removed by distillation under reduced pressure. The oily residue which was not further purified showed in the infrared spectrum a strong carbonyl band at 1730 cm-1.

Workup

  1. temperatureThe solution was cooled
  2. filtrationfiltered with suction
  3. customto remove the precipitate
  4. customthe filtrate was evaporated to dryness at 0.1 mm Hg
  5. dissolutionThe residue was dissolved in ether
  6. washwashed with H2O
  7. dry with materialdried over MgSO4
  8. customthe solvent was removed by distillation under reduced pressure
  9. customThe oily residue which was not further purified

Sources & evidence

ORD record
ord-e8ab5674cd3d4f94abe457b6bc99f456
Source dataset
uspto-grants-1978_07
Patent number
US04098815

Reaction notes

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