Hydrochloric Acid → 4-((E)-2-fluorovinyl)-4'-((E)-prop-1-en-1-yl)-1,1'-bi(cyclohexane)

HRID 1614841Notes

Reaction equation

HRID 1614841 reaction equation
[F:1][C:2](F)=[CH:3][CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][CH:13](/[CH:16]=[CH:17]/[CH3:18])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1.C1(C)C=CC=CC=1.[H-].[H-].COCCO[Al+]OCCOC.[Na+].Cl>C1(C)C=CC=CC=1>[F:1]/[CH:2]=[CH:3]/[CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][CH:13](/[CH:16]=[CH:17]/[CH3:18])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67340441Sodium bis(2-methoxyethoxy)aluminum hydride tolueneHCID 71009768(E)-4-(2,2-difluorovinyl)-4'-(prop-1-en-1-yl)-1,1'-bi(cyclohexane)

Product 1

HCID 710098004-((E)-2-fluorovinyl)-4'-((E)-prop-1-en-1-yl)-1,1'-bi(cyclohexane)

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound (1-B) (5.0 g) obtained in the above operation was dissolved in toluene (50 ml), and a 65% sodium bis(2-methoxyethoxy)aluminum dihydride toluene solution (8.0 ml) was added dropwise. After completion of the reaction, 1N hydrochloric acid was added, and extraction was carried out with toluene. An organic layer was washed with a saturated aqueous solution of sodium chloride, a saturated aqueous solution of sodium hydrogencarbonate and water, and then the resultant solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and thus a colorless oily matter was obtained. The resultant material was subjected to silica gel column chromatography (heptane) and recrystallization at a low temperature by using Solmix A-11 (registered trademark) (Japan Alcohol Trading Co., Ltd.), and thus compound (1-1) was obtained as a colorless oily matter (1.2 g).

Workup

  1. additionwas added
  2. extractionextraction
  3. washAn organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, and then the resultant solution was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthus a colorless oily matter was obtained
  7. customThe resultant material was subjected to silica gel column chromatography (heptane) and recrystallization at a low temperature

Sources & evidence

ORD record
ord-85f02fecb0b2456e83588bd8ba8316de
Source dataset
uspto-grants-2014_07
Patent number
US08765011B2

Reaction notes

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