Hydrochloric Acid → HCID 23451708, compound

HRID 1278449Notes

Reaction equation

HRID 1278449 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7](=[C:10]1[CH2:14][CH2:13][C:12]2([CH:19]([CH3:20])[CH2:18][C:17]([O:21]C(C)C)=[CH:16][C:15]2=O)[CH2:11]1)([CH3:9])[CH3:8].O.Cl>CCOCC>[C:7](=[C:10]1[CH2:14][CH2:13][C:12]2([CH:19]([CH3:20])[CH2:18][C:17](=[O:21])[CH:16]=[CH:15]2)[CH2:11]1)([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 23451695HCID 23451695, compound

Product 1

HCID 23451708HCID 23451708, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred suspension of lithium aluminum hydride (0.15 g, 4 mmol) in anhydrous ether (10 ml) was added 2-isopropylidene-8-isopropoxy-10-methylspiro[4.5]dec-7-en-6-one (2 g, 8 mmol), prepared according to Example 2. The mixture was heated at reflux for 1 hour and water cautiously added. The solution was mixed with 10% hydrochloric acid (30 mL) and agitated at room temperature for 45 minutes. The aqueous mixture was extracted with ether and the ether extracts washed with saturated sodium bicarbonate solution and dried (Na2SO4). The solution was concentrated and the crude ketone kugelrohr distilled to give 1.4 g, bp 130°/0.5 mm, of enone having the structure: ##STR26##

Workup

  1. customprepared
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 1 hour
  4. extractionThe aqueous mixture was extracted with ether
  5. washthe ether extracts washed with saturated sodium bicarbonate solution
  6. dry with materialdried (Na2SO4)
  7. concentrationThe solution was concentrated
  8. distillationthe crude ketone kugelrohr distilled
  9. customto give 1.4 g, bp 130°/0.5 mm

Sources & evidence

ORD record
ord-bd95af5f15864a3bbff8c6c1c8ef4f6e
Source dataset
uspto-grants-1981_07
Patent number
US04281204

Reaction notes

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