Hydrochloric Acid → HCID 23451711, compound

HRID 1278450Notes

Reaction equation

HRID 1278450 reaction equation
[Mg].[CH2:2](Br)[CH3:3].[C:5](=[C:8]1[CH2:12][CH2:11][C:10]2([CH:17]([CH3:18])[CH2:16][C:15]([O:19]C(C)C)=[CH:14][C:13]2=O)[CH2:9]1)([CH3:7])[CH3:6].Cl>CCOCC>[C:5](=[C:8]1[CH2:12][CH2:11][C:10]2([CH:17]([CH3:18])[CH2:16][C:15](=[O:19])[CH:14]=[C:13]2[CH2:2][CH3:3])[CH2:9]1)([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 5462224MagnesiumHCID 23451695HCID 23451695, compound

Product 1

HCID 23451711HCID 23451711, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A Grignard solution was prepared from magnesium (1.17 g, 0.048 g-atom) and ethyl bromide (5.2 g, 0.048 mol) in anhydrous ether (50 mL) under nitrogen. 2-Isopropylidene-8-isopropoxy-10-methylspiro[4.5]dec-7-en-6-one (4 g, 0.015 mol), prepared according to Example 2, in anhydrous ether (20 mL) was added dropwise at room temperature and the mixture then heated at reflux for 4 hours. The solution was cautiously added to 2 N hydrochloric acid (200 mL) and stirred for 1 hour at room temperature. The mixture was extracted with ether and the ether extracts washed with saturated sodium bicarbonate, brine, and dried (Na2SO4). Kugelrohr distillation afforded

Workup

  1. additionwas added dropwise at room temperature
  2. temperaturethe mixture then heated
  3. temperatureat reflux for 4 hours
  4. extractionThe mixture was extracted with ether
  5. washthe ether extracts washed with saturated sodium bicarbonate, brine
  6. dry with materialdried (Na2SO4)
  7. distillationKugelrohr distillation
  8. customafforded

Sources & evidence

ORD record
ord-97c195106bd1453ea7c8d6f7ae85e380
Source dataset
uspto-grants-1981_07
Patent number
US04281204

Reaction notes

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