Water → Ethyl (6-cyano-1,2,3,4-tetrahydro-1-naphthalenyl)acetate

HRID 978761Notes

Reaction equation

HRID 978761 reaction equation
[H-].[Na+].O=[C:4]1[CH2:13][CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([C:14]#[N:15])[CH:7]=[CH:6][C:5]1=2.[OH2:16].[O:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>C(O)C.[C].[Pd]>[C:14]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH:4]([CH2:19][C:18]([O:17][CH2:21][CH3:20])=[O:16])[CH2:13][CH2:12][CH2:11]2)#[N:15]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 108991325-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 13882836Ethyl (6-cyano-1,2,3,4-tetrahydro-1-naphthalenyl)acetate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

2.75 g of 50% sodium hydride was suspended in 120 ml of tetrahydrofuran and 14.5 g of triethyl phosphonoacetate was added thereto. The mixture was stirred at room temperature for 15 minutes and 10.2 g of 5-oxo-5,6,7,8-tetrahydro-2-naphthonitrile was added thereto. The resulting mixture was heated under reflux for 1 hour. After cooling, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water and dried and then concentrated in vacuo. The residue was purified by column chromatography on 100 g of silica gel to give an oily product. The product was dissolved in 80 ml of ethanol and 1.5 g of 10% palladium carbon was added thereto. The mixture was catalytically reduced. After absorption of hydrogen gas was completed, the catalyst was removed by filtration. The filtrate was concentrated in vacuo to give 12.1 g of ethyl 2-(6-cyano-1,2,3,4-tetrahydro-1-naphthyl)acetate as crystals with m.p. 45°-47° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on 100 g of silica gel
  9. customto give an oily product
  10. customAfter absorption of hydrogen gas
  11. customthe catalyst was removed by filtration
  12. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-65ec5af468e347559bb212e3f2cd94a1
Source dataset
uspto-grants-1987_05
Patent number
US04665188

Reaction notes

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