Diethyl Ether → HCID 21186846, compound

HRID 1384410Notes

Reaction equation

HRID 1384410 reaction equation
[Mg].Br[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[CH3:13][CH:14]([CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH2:15][CH2:16][O:17][CH2:18][C:19]#N.CC[O:29]CC>>[CH3:13][CH:14]([CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH2:15][CH2:16][O:17][CH2:18][C:19]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)=[O:29]

Participants

5

Reactant 4

HCID 3283Diethyl Ether3×HCID 113722-BromonaphthaleneHCID 5462224MagnesiumHCID 11788816HCID 11788816, compound

Product 1

HCID 21186846HCID 21186846, compound

Conditions

Temperature
2.5 °C

Procedure

To a suspension of 2.24 g of magnesium in ether, a solution of 19.09 g 2-bromonaphthalene in 80 ml of ether was dropped. The mixture was heated to reflux. After refluxing for one hour, the mixture was cooled to 0-5° C. and a solution of 15.00 g (3,7-dimethyl-oct-6-enyloxy)-acetonitrile (Kulka, K. et al., Perfumer & Flavorist Vol. 3 (1978), p.39) in 20 ml of ether was dropped in at this temperature. After stirring at room temperature for 3 hours, the mixture was quenched with water and aqueous sulfuric acid. After extracting with ether, the combined organic phases were washed with saturated sodium bicarbonate and water, dried, filtered, and evaporated to dryness. The resulting dark oil was purified by chromatography to yield 15.22 g of a yellow oil.

Workup

  1. temperatureThe mixture was heated to reflux
  2. temperatureAfter refluxing for one hour
  3. customthe mixture was quenched with water and aqueous sulfuric acid
  4. extractionAfter extracting with ether
  5. washthe combined organic phases were washed with saturated sodium bicarbonate and water
  6. customdried
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe resulting dark oil was purified by chromatography

Sources & evidence

ORD record
ord-e1a7a257437c4504b5b198679880b9c8
Source dataset
uspto-grants-2001_07
Patent number
US06258854B1

Reaction notes

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