Diethyl Ether → HCID 178505681, compound

HRID 2050441Notes

Reaction equation

HRID 2050441 reaction equation
[Br-].[F:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.[O:29]1[CH2:33][CH2:32][O:31][CH:30]1[CH2:34][CH2:35][C@H:36]1[CH2:41][CH2:40][C@H:39]([C@H:42]2[CH2:47][CH2:46][C@H:45]([CH:48]=O)[CH2:44][CH2:43]2)[CH2:38][CH2:37]1.C(OCC)C>COC(C)(C)C>[O:29]1[CH2:33][CH2:32][O:31][CH:30]1[CH2:34][CH2:35][C@H:36]1[CH2:41][CH2:40][C@H:39]([C@H:42]2[CH2:47][CH2:46][C@H:45]([CH:48]=[CH:7][C:6]3[CH:5]=[CH:4][C:3]([F:2])=[CH:28][CH:27]=3)[CH2:44][CH2:43]2)[CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10837295(4-Fluorobenzyl)triphenylphosphonium bromideHCID 178520951HCID 178520951, compound

Product 1

HCID 178505681HCID 178505681, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

3 g of p-fluorobenzyl-triphenylphosphonium bromide (preparable from p-fluorobenzyl bromide and triphenylphosphine) are suspended in 50 ml of tert.butyl methyl ether. The suspension is treated at room temperature with 0.75 g of potassium tert.butylate and stirred for 1.5 hours. Subsequently, the mixture is treated dropwise at 0° C. within 5 minutes with a solution of 1.40 g of trans-4-[trans-4-[2-(1,3-dioxolan-2-yl)ethyl]cyclohexyl]cyclohexanecarboxaldehyde in 25 ml of tert.butyl methyl ether and stirred at room temperature for a further 24 hours. Thereafter, the reaction mixture is taken up diethyl ether, washed several times with water, dried over magnesium sulfate, filtered and concentrated. Chromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether (vol. 3:97) gives β-[trans-4-[trans-4-(2-(1,3-dioxolan-2-yl)ethyl)cyclohexyl]cyclohexyl]-4-fluorostyrene.

Workup

  1. stirringstirred at room temperature for a further 24 hours
  2. washwashed several times with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customChromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether (vol. 3:97)

Sources & evidence

ORD record
ord-acd5775212004195b1abf4dde7f81def
Source dataset
uspto-grants-1991_05
Patent number
US05013477

Reaction notes

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