Hydrochloric Acid → HCID 54325886, compound

HRID 263144Notes

Reaction equation

HRID 263144 reaction equation
[N+:1]([CH2:4][CH:5]1[CH2:13][C:8]2(OCC[O:9]2)[CH:7]([CH2:14][CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:6]1[CH:23]=[CH:24][C:25]([CH3:32])([OH:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([O-:3])=[O:2].O1CCCC1.Cl>O>[OH:31][C:25]([CH3:32])([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:24]=[CH:23][CH:6]1[CH:5]([CH2:4][N+:1]([O-:3])=[O:2])[CH2:13][C:8](=[O:9])[CH:7]1[CH2:14][CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 54508268HCID 54508268, compound

Product 1

HCID 54325886HCID 54325886, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.20 g. of 7-[8-nitromethyl-7-(3-methyl-3-hydroxy-1-octenyl)-1,4-dioxaspiro[4.4]non-6-yl]-5-heptenoic acid in 4 ml. of tetrahydrofuran was treated at 0° C. with 0.4 ml. of concentrated hydrochloric acid and stirred at 0° C. for 1.5 hours. The reaction mixture was added to water and extracted with ether. After washing with water and drying over magnesium sulfate, the extract was evaporated and the residue chromatographed on silica. Elution with 15% ethyl acetate in hexane gave 0.11 g. of the title product as an oil, λmaxfilm 3.00 (shoulder), 3.50, 5.80, 6.45, 7.25, 10.30μ. NMR: δ 1.32 (S, 15-methyl), 4.49 (M, 2, --CH2NO2), 5.80 (M, 4, olefinic --H), 5.92 (S, 2, OH) ppm. Mass spectrum: M+ --H2O at m/e 391.2402 (theory 391.2358).

Workup

  1. extractionextracted with ether
  2. washAfter washing with water
  3. dry with materialdrying over magnesium sulfate
  4. customthe extract was evaporated
  5. customthe residue chromatographed on silica
  6. washElution with 15% ethyl acetate in hexane
  7. customgave 0.11 g

Sources & evidence

ORD record
ord-205531bfaae548a1ac13d15ccb690ae8
Source dataset
uspto-grants-1979_05
Patent number
US04156094

Reaction notes

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