Diethyl Ether → HCID 178418606, compound

HRID 5304Notes

Reaction equation

HRID 5304 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3C=C[C:34]([C:37]#N)=[CH:33][CH:32]=3)=[CH:27][CH:26]=2)[CH2:21][CH2:20]1.[C:39](=[O:42])([O-])[O-].[Na+].[Na+].[CH2:45](OCC)C>O1CCCC1>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:18][C@H:19]1[CH2:20][CH2:21][C@H:22]([C:25]2([C:39](=[O:42])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:30]=[CH:29][C:28]([C:31]3[CH:45]=[CH:37][CH:34]=[CH:33][CH:32]=3)=[CH:27][CH2:26]2)[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 178418638HCID 178418638, compoundHCID 178418655HCID 178418655, compound

Product 1

HCID 178418606HCID 178418606, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of nonylmagnesium bromide (8.3 mmol) in 30 ml of diethyl ether was treated at 0° C. with a solution of 1.5 g of trans-4-(4'-cyano-4-biphenylyl)cyclohexyl tetrahydropyranyl ether in 15 ml of tetrahydrofuran. The reaction mixture was heated at slight reflux overnight and then treated with dilute sodium carbonate solution. The organic phase was separated and the aqueous phase was back-extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed once with dilute sodium carbonate solution and twice with water and then dried over magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). The trans-4-(4-decanoyl-4-biphenylyl)cyclohexyl tetrahydropyranyl ether (1.8 g) obtained was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat slight reflux overnight
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was back-extracted three times with 50 ml of diethyl ether each time
  5. washThe combined organic phases were washed once with dilute sodium carbonate solution and twice with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1)

Sources & evidence

ORD record
ord-5ec990aeb1174b278ed38ed7122071bb
Source dataset
uspto-grants-1993_09
Patent number
US05244597

Reaction notes

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