Dichloromethane → HCID 178445815, compound

HRID 2254979Notes

Reaction equation

HRID 2254979 reaction equation
[CH:1](/[C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1)=[CH:2]\[CH2:3][CH3:4].C1(N=C=NC2CCCCC2)CCCCC1.[CH:29](/[C@H:33]1[CH2:38][CH2:37][C@H:36](O)[CH2:35][CH2:34]1)=[CH:30]\[CH2:31][CH3:32].C(Cl)Cl>CN(C)C1C=CN=CC=1.CCCCCC>[CH:29](/[C@H:33]1[CH2:38][CH2:37][C@H:36]([O:12][C:11]([C@H:8]2[CH2:9][CH2:10][C@H:5](/[CH:1]=[CH:2]/[CH2:3][CH3:4])[CH2:6][CH2:7]2)=[O:13])[CH2:35][CH2:34]1)=[CH:30]\[CH2:31][CH3:32]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 178445660HCID 178445660, compoundHCID 178445813HCID 178445813, compound

Product 1

HCID 178445815HCID 178445815, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8058HexaneSolvent

Procedure

A mixture of 200 mg of trans-4-(1E-butenyl)cyclohexanecarboxylic acid, 272.4 mg of dicyclohexylcarbodimide, 13.4 mg of 4-(dimethylamino)pyridine, 169.7 mg of trans-4-(1E-butenyl)cyclohexanol and 4 ml of methylene chloride was stirred at room temperature for 21 hours while gassing with argon. Subsequently, the heterogeneous reaction mixture was diluted with 10 ml of hexane and filtered (rinsing with hexane). The concentrated filtrate was taken up in 30 ml of hexane and the solution was washed in each case once with 30 ml of 5 percent hydrochloric acid, 30 ml of saturated sodium hydrogen carbonate solution and 30 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the colourless oil (450 mg) on silica gel with ethyl acetate/petroleum ether (vol. 1:99) gave 280 mg (80.1%) of trans-4-(1E-butenyl)cyclohexanecarboxylic acid trans-4-(1E-butenyl)cyclohexyl ester as colourless crystals. Recrystallization from 15 ml of methanol at - 20° C. gave 223 mg of ester as colourless needles with melting point (C-N) 46.3° C. and cl.p. (N-I) 58.7° C.

Workup

  1. filtrationfiltered
  2. wash(rinsing with hexane)
  3. washthe solution was washed in each case once with 30 ml of 5 percent hydrochloric acid, 30 ml of saturated sodium hydrogen carbonate solution and 30 ml of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-df8d5edd0a75406c97432a680ce37050
Source dataset
uspto-grants-1993_08
Patent number
US05238602

Reaction notes

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