Toluene → HCID 178444588, compound

HRID 2399187Notes

Reaction equation

HRID 2399187 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][C:13](=[CH:16][O:17][CH3:18])[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH:19](/[CH:24](CO)[CH2:25][OH:26])=[CH:20]\[CH2:21][CH2:22][CH3:23].C1(C)C=CC=CC=1>S(=O)(=O)(O)O.O>[F:1][C:2]1[CH:9]=[C:8]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C@H:16]3[O:26][CH2:25][C@H:24](/[CH:19]=[CH:20]/[CH2:21][CH2:22][CH3:23])[CH2:18][O:17]3)[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 1140TolueneHCID 137104072-Fluoro-4-[4-(methoxymethylidene)cyclohexyl]benzonitrileHCID 151424932-(1E-pentenyl)-1,3-propanediol

Product 1

HCID 178444588HCID 178444588, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

A mixture of 0.98 g of 2-fluoro-4-[4-(methoxymethylidene)cyclohexyl]benzonitrile (U.S. Pat. No. 4,784,471), 0.70 g of 2-(1E-pentenyl)-1,3-propanediol, 45 ml of toluene, 2 ml of water and 10 drops of 10 percent sulphuric acid was stirred at about 85° C. for 75 minutes, then heated to boiling for 1 hour, whereby moist solvent distilled off and was replaced by fresh toluene. The reaction mixture was treated with 12 drops of triethylamine and, after cooling, washed three times with 15 ml of water, dried over sodium sulphate, filtered and concentrated. Chromatography of the residue (1.86 g) on 50 g of silica gel with hexane/ethyl acetate (vol. 9:1) and two-fold recrystallization from 8 ml of hexane each time gave 0.65 g of pure 2-fluoro-4-[trans-4-[trans-5-(1E-pentenyl)-1,3-dioxan-2-yl]cyclohexyl]benzonitrile, m.p. (C-N) 91.2° C., cl.p. (N-I) 192.5° C.

Workup

  1. temperatureheated
  2. distillationwhereby moist solvent distilled off
  3. additionThe reaction mixture was treated with 12 drops of triethylamine
  4. temperatureafter cooling
  5. washwashed three times with 15 ml of water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customChromatography of the residue (1.86 g) on 50 g of silica gel with hexane/ethyl acetate (vol. 9:1) and two-fold recrystallization from 8 ml of hexane each time

Sources & evidence

ORD record
ord-f7b75e01f7c0407798ef8527dd9cf566
Source dataset
uspto-grants-1995_09
Patent number
US05447658

Reaction notes

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