Diethyl Ether → 2-(5-ethoxyhept-1-yl)bicyclo[3.3.0]octan-7-one 4-(5-ethoxyheptyl)hexahydro-2(1H)-pentalenone

HRID 1722363Notes

Reaction equation

HRID 1722363 reaction equation
[N+](=C)=[N-].CCOCC.[CH2:9]([O:11][CH:12]([CH2:26][CH3:27])[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[CH2:24][CH2:23][CH:22]2[CH:18]1[CH2:19][C:20](=[O:25])[CH2:21]2)[CH3:10].COC(CC)CCCCC1CCC2C1CC(=O)C2>C(O)(=O)C.[Zn]>[CH2:9]([O:11][CH:12]([CH2:26][CH3:27])[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[CH2:24][CH2:23][CH:22]2[CH:18]1[CH2:19][C:20](=[O:25])[CH2:21]2)[CH3:10].[CH2:9]([O:11][CH:12]([CH2:26][CH3:27])[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[CH2:24][CH2:23][CH:22]2[CH:18]1[CH2:19][C:20](=[O:25])[CH2:21]2)[CH3:10]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 55994CioteronelHCID 104007392(1H)-Pentalenone, 4-(5-ethoxyheptyl)hexahydro-

Product 1

HCID 200287092-(5-ethoxyhept-1-yl)bicyclo[3.3.0]octan-7-one 4-(5-ethoxyheptyl)hexahydro-2(1H)-pentalenone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
70 °C

Procedure

After 50 minutes the excess diazomethane is neutralized with the addition of acetic acid (10 ml). The solvent is removed under vacuum leaving a clear yellow liquid. The crude product is then diluted with acetic acid (240 ml) and stirred while zinc powder (72 g, 1.10 moles) is slowly added. The reaction is heated in a 70° C. water bath for 1 hour, after which time ether (500 ml) is added and the solution filtered. The ether layer is washed with brine (100 ml) and then with a solution of saturated bicarbonate. The ether layer is separated and dried over sodium sulfate. The solvent is removed under vacuum leaving a clear yellow oil. The crude 2-(5-ethoxyhept-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone} is chromatographed on silica gel and subsequently kugelrohred under vacuum leaving compound VI as a clear, colorless oil (12 g, 0.045 moles).

Workup

  1. customThe solvent is removed under vacuum
  2. customleaving a clear yellow liquid
  3. additionis slowly added
  4. filtrationthe solution filtered
  5. washThe ether layer is washed with brine (100 ml)
  6. customThe ether layer is separated
  7. dry with materialdried over sodium sulfate
  8. customThe solvent is removed under vacuum
  9. customleaving a clear yellow oil
  10. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-5586ed485caa4d9b8f9c63a598b19c31
Source dataset
uspto-grants-1989_08
Patent number
US04855322

Reaction notes

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