Tetrahydrofuran → 1-(4-(1,3-Dioxan-2-yl)-2-butenyl)-4-(4-cyanophenyl)cyclohexane

HRID 975741Notes

Reaction equation

HRID 975741 reaction equation
O1CCCC1.[Br-].[O:7]1[CH2:12][CH2:11][CH2:10][O:9][CH:8]1[CH2:13][CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[C:40]([C:42]1[CH:47]=[CH:46][C:45]([CH:48]2[CH2:53][CH2:52][CH:51]([CH2:54][CH:55]=O)[CH2:50][CH2:49]2)=[CH:44][CH:43]=1)#[N:41]>CCOCC>[O:9]1[CH2:10][CH2:11][CH2:12][O:7][CH:8]1[CH2:13][CH:14]=[CH:55][CH2:54][CH:51]1[CH2:50][CH2:49][CH:48]([C:45]2[CH:44]=[CH:43][C:42]([C:40]#[N:41])=[CH:47][CH:46]=2)[CH2:53][CH2:52]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 27241682-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromideHCID 18651095trans-4-(4-Cyanophenyl)cyclohexylacetaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 541490471-(4-(1,3-Dioxan-2-yl)-2-butenyl)-4-(4-cyanophenyl)cyclohexaneYield 50%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Tetrahydrofuran (100 ml) was added to 2-(1,3-dioxan-2-yl)ethyltriphenylphosphonium bromide (19.2 g, 42 mmols), followed by suspending, stirring under ice cooling till the liquid temperature reached 10° C. The reaction mixture was added potassium t-butoxide (4.7 g, 42 mmols), followed by elevating the temperature up to room temperature under ice cooling for one hour, stirring for one hour, dropwise adding a tetrahydrofuran (20 ml) solution of 2-(4-(4-cyanophenyl)cyclohexyl)acetaldehyde (9.0 g, 40 mmols) over 30 minutes from the dropping funnel, further stirring the reaction mixture for 5 hours after completion of the dropwise addition, adding ether (100 ml), allowing to stand for one hour, filtering off deposited insoluble substance, concentrating the filtrate under reduced pressure and isolating and purifying the resulting pale brown oil by means of silica gel column chromatography, to obtain white solids (6.8 g, 20 mmols) of 1-(4-(1,3-dioxan-2-yl)-2-butenyl)-4-(4-cyanophenyl)cyclohexane.

Workup

  1. customreached 10° C
  2. customup to room temperature
  3. customfor one hour
  4. stirringstirring for one hour
  5. stirringfurther stirring the reaction mixture for 5 hours
  6. additionafter completion of the dropwise addition
  7. filtrationfiltering off
  8. concentrationconcentrating the filtrate under reduced pressure
  9. customisolating
  10. custompurifying the resulting pale brown oil by means of silica gel column chromatography

Sources & evidence

ORD record
ord-b1a2d7a0e32642668dd110b1fb8a19bc
Source dataset
uspto-grants-1997_03
Patent number
US05609791

Reaction notes

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