Triethylamine → HCID 178460482, compound

HRID 2392593Notes

Reaction equation

HRID 2392593 reaction equation
C(N([CH2:6][CH3:7])CC)C.CS(Cl)(=O)=O.[C:13]([O:17][CH2:18][CH2:19][CH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([C@H:27]2[CH2:32][CH2:31][C@H:30]([C:33]([OH:35])=[O:34])[CH2:29][CH2:28]2)[CH2:23][CH2:22]1)(=[O:16])[CH:14]=[CH2:15].O[C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[OH:45])[C:40]#[N:41]>CN(C)C1C=CN=CC=1.O.O1CCCC1>[C:13]([O:17][CH2:18][CH2:19][CH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([C@H:27]2[CH2:28][CH2:29][C@H:30]([C:33]([O:35][C:37]3[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=3[O:45][C:33]([C@H:30]3[CH2:29][CH2:28][C@H:27]([C@H:24]4[CH2:25][CH2:26][C@H:21]([CH2:20][CH2:19][CH2:18][O:17][C:13](=[O:16])[CH:6]=[CH2:7])[CH2:22][CH2:23]4)[CH2:32][CH2:31]3)=[O:34])[C:40]#[N:41])=[O:34])[CH2:31][CH2:32]2)[CH2:23][CH2:22]1)(=[O:16])[CH:14]=[CH2:15]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 870653,4-DihydroxybenzonitrileHCID 178460483HCID 178460483, compound

Product 1

HCID 178460482HCID 178460482, compoundYield 71.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

0.9 g of triethylamine and then 0.5 g of methanesulphonyl chloride were added dropwise at -25° C. while stirring to a solution of 2.0 g of trans-4-(trans-4-[3-acryloyloxypropyl]cyclohexyl)-cyclohexanecarboxylic acid and 40 ml of tetrahydrofuran. The reaction mixture was stirred at -25° C. for 1 hour, then treated with 0.28 g of 3,4-dihydroxybenzonitrile and 0.05 g of 4-(dimethylamino)pyridine, stirred at room temperature overnight, poured into 100 ml of water and then extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate, filtered and subsequently concentrated. Chromatographic purification of the residue on silica gel with cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from a cyclohexane/ethyl acetate mixture (vol. 8:2) of the fractions which were pure according to thin-layer chromaography gave 1.1 g of 3,4-bis[trans-4-(trans-4-[3-acryloyloxypropyl]cyclohexyl)-cyclohexanecarbonyloxy]benzonitrile.

Workup

  1. stirringstirred at room temperature overnight
  2. extractionextracted three times with 50 ml of diethyl ether each time
  3. washThe combined organic phases were washed twice with 100 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationsubsequently concentrated
  7. customChromatographic purification of the residue on silica gel
  8. customwith cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from a cyclohexane/ethyl acetate mixture (vol. 8:2) of the fractions which

Sources & evidence

ORD record
ord-bf2238f7ea9443edbc54222c54dade02
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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