Hydrochloric Acid → HCID 178442116, compound

HRID 1893072Notes

Reaction equation

HRID 1893072 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]=[CH:18][CH:19]3[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:21][CH2:20]3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=O.COCCO[AlH2-]OCCOC.[Na+].O.Cl>C1(C)C=CC=CC=1>[CH2:25]([CH:22]1[CH2:21][CH2:20][CH:19]([CH:18]=[CH:17][C:14]2[CH:13]=[CH:12][C:11]([C@H:8]3[CH2:7][CH2:6][C@H:5]([CH:3]=[O:2])[CH2:10][CH2:9]3)=[CH:16][CH:15]=2)[CH2:24][CH2:23]1)[CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 16684438Red-AlHCID 584532174-{4-[2-(4-Pentyl-cyclohexyl)-ethenyl]-phenyl}cyclohexane carboxylic acid methyl ester

Product 1

HCID 178442116HCID 178442116, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-40 °C

Procedure

Vitride (3.3M in toluene, 10 eq, 26.6 ml, 87.7 mmol) was added with syringe to a flask filled with Argon gas at 0° C., and morpholine (10 eq, 7.67 ml, 87.7 mmol) was added slowly dropwise with syringe. Then, toluene (a half of morpholine mmol, 44 ml) was added dropwise with syringe to produce vitride solution. 88 ml of a solution including cyclohexane carboxylate compound (3.48 g, 8.77 mmol) obtained in Example 4-1 in toluene a solution was added to another 2-neck flask filled with argon gas, and vitride solution was added slowly dropwise at −70° C. for 30 minutes. Then, the solution was stirred with maintaining −30 to −50° C. for 6 hours and water was added very slowly dropwise to the flask. 1M HCl was slowly added to the flask to neutralize the reaction solution. White precipitate was filtered under reduced pressure and the filtrate was extracted by toluene (20 ml×three times). The organic layer was collected, washed by distilled water (10 ml×two times), dried with anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane:ether=5:1, Rf=0.32) to produce 1.77 g (55%) of trans-4-{4-[2-(4-pentylcyclohexyl)ethenyl]phenyl}cyclohexane carbaldehyde.

Workup

  1. additionwas added to another 2-neck flask
  2. additionwas added slowly dropwise at −70° C. for 30 minutes
  3. filtrationWhite precipitate was filtered under reduced pressure
  4. extractionthe filtrate was extracted by toluene (20 ml×three times)
  5. customThe organic layer was collected
  6. washwashed
  7. distillationby distilled water (10 ml×two times)
  8. dry with materialdried with anhydrous Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained residue was purified by column chromatography (hexane:ether=5:1, Rf=0.32)

Sources & evidence

ORD record
ord-e0c39d9b4e0243b48a9545c895b02ecc
Source dataset
uspto-grants-2013_08
Patent number
US08512598B2

Reaction notes

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