tert-Butyl methyl ether → HCID 178444326, compound

HRID 653373Notes

Reaction equation

HRID 653373 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16][CH:17]=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].CO[C:21](C)(C)[CH3:22]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[CH2:15]([C@H:12]1[CH2:13][CH2:14][C@H:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:10][CH2:11]1)[CH2:16][CH:17]=[CH:21][CH3:22]

Participants

4

Reactant 2

HCID 15413tert-Butyl methyl ether2×HCID 178509797HCID 178509797, compound

Product 1

HCID 178444326HCID 178444326, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst

Procedure

A suspension of 14.8 g of ethyltriphenylphosphonium bromide in 150 ml of t-butyl methyl ether was treated with 4.54 g of solid potassium t-butylate at -10° C. within 5 minutes while gassing with argon in a sulphonation flask provided with a mechanical stirrer. The suspension was stirred at room temperature for 1 hour, then treated dropwise at 0° C. within 5 minutes with a solution of 6.4 g of 3-[trans-4-(p-cyanophenyl)cyclohexyl]propionaldehyde in 40 ml of t-butyl methyl ether and stirred at room temperature for a further 15 hours. The mixture was subsequently partitioned three times in diethyl ether/water. The organic extracts were washed twice with water, dried over magnesium sulphate, filtered and concentrated. In order to separate triphenylphosphine oxide, the residue was dissolved in ethyl acetate and the solution was diluted with petroleum ether, filtered and concentrated. Chromatographic separation of the resulting, yellowish oil (8.55 g) on silica gel with ethyl acetate/petroleum ether (vol. 3:97) gave 5.93 g (89%) of p-[trans-4-(3-pentenyl)cyclohexyl]benzonitrile as white crystals.

Workup

  1. customwhile gassing with argon in a sulphonation flask
  2. customprovided with a mechanical stirrer
  3. stirringstirred at room temperature for a further 15 hours
  4. customThe mixture was subsequently partitioned three times in diethyl ether/water
  5. washThe organic extracts were washed twice with water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customIn order to separate triphenylphosphine oxide
  10. dissolutionthe residue was dissolved in ethyl acetate
  11. additionthe solution was diluted with petroleum ether
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customChromatographic separation of the resulting, yellowish oil (8.55 g) on silica gel with ethyl acetate/petroleum ether (vol. 3:97)

Sources & evidence

ORD record
ord-451a64abd63a4fae9be481670346d532
Source dataset
uspto-grants-1987_06
Patent number
US04676604

Reaction notes

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