Sulfuric Acid → HCID 13924084, compound

HRID 1789528Notes

Reaction equation

HRID 1789528 reaction equation
[CH:1]1CC(C(CC)CC=O)C[CH:5]=1.[CH:12]1([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[O:22])[CH2:16][CH2:15][CH:14]=[CH:13]1.C([Mg]Br)C.S(=O)(=O)(O)O>O.O1CCCC1>[OH:22][CH:21]([CH2:1][CH3:5])[CH2:20][CH2:19][CH2:18][CH2:17][CH:12]1[CH2:16][CH2:15][CH:14]=[CH:13]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 15053016HCID 15053016, compoundHCID 20028703HCID 20028703, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 13924084HCID 13924084, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

All work is performed an inert atmosphere using anhydrous tetrahydrofuran. The starting material, 3-(5-cyclopenten-3-yl) valeraldehyde {2-cyclopentene-1-pentanal} (75 g, 0.493 moles) is diluted in tetrahydrofurar (750 ml) and cooled in a -30° C. ethanol/dry ice bath. Ethyl magnesium bromide (0.493 moles) is added dropwise to the stirring reaction mixture for a period of over 2 hours. The mixture is warmed to 0° C. and water (100 ml), followed by 15% sulfuric acid (200 ml), is added and the organic phase separated. The aqueous layer is extracted with ether (2×300 ml) and the organic extracts are combined. The volume is reduced and the residue washed with brine (400 ml). The product is dried over anhydrous sodium sulfate and the remaining solvent removed under vacuum leaving a clear yellow oil. The crude product is chromatographed on silica gel and subsequently kugelrohred under vacuum leaving clear, colorless oil (10.2 g, 0.056 moles).

Workup

  1. additionis diluted in tetrahydrofurar (750 ml)
  2. temperatureThe mixture is warmed to 0° C.
  3. additionis added
  4. customthe organic phase separated
  5. extractionThe aqueous layer is extracted with ether (2×300 ml)
  6. washthe residue washed with brine (400 ml)
  7. dry with materialThe product is dried over anhydrous sodium sulfate
  8. customthe remaining solvent removed under vacuum
  9. customleaving a clear yellow oil
  10. customThe crude product is chromatographed on silica gel
  11. customleaving clear

Sources & evidence

ORD record
ord-572be6f88f034fd7920d4ba2775bac75
Source dataset
uspto-grants-1987_08
Patent number
US04689349

Reaction notes

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