Dicyclohexylcarbodiimide → HCID 178455793, compound

HRID 370702Notes

Reaction equation

HRID 370702 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1)#[CH:2].[CH2:12]([C@H:17]1[CH2:22][CH2:21][C@H:20](O)[CH2:19][CH2:18]1)[CH2:13][CH2:14][CH2:15][CH3:16].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:12]([C@H:17]1[CH2:18][CH2:19][C@H:20]([O:10][C:9]([C@H:6]2[CH2:7][CH2:8][C@H:3]([C:1]#[CH:2])[CH2:4][CH2:5]2)=[O:11])[CH2:21][CH2:22]1)[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 178444573HCID 178444573, compoundHCID 178455788HCID 178455788, compound

Product 1

HCID 178455793HCID 178455793, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 122 mg of trans-4-ethynylcyclohexanecarboxylic acid, 145 mg of trans-4-pentylcyclohexanol, 206 mg of dicyclohexylcarbodiimide and 12.2 mg of 4-(dimethylamino)pyridine in 10 ml of methylene chloride was stirred at room temperature for 21 hours. The separated white precipitate was filtered off, the filtrate was poured into 50 ml of water and extracted three times with 50 ml of methylene chloride each time. The organic phases were washed once with 50 ml of water, twice with 30 ml of 5% aqueous acetic acid each time and twice with 30 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue on silica gel with 5% ethyl acetate/petroleum ether gave 159 mg (65%) of trans-4-ethynylcyclohexanecarboxylic acid trans-4-pentylcyclohexyl ester as a colourless crystallizing oil. Additional crystallization from isopropanol at -20° C. yielded and analytically pure ester; m.p. (C-I) 54.2° C., cl.p. (N-I) 40.5° C.

Workup

  1. filtrationThe separated white precipitate was filtered off
  2. additionthe filtrate was poured into 50 ml of water
  3. extractionextracted three times with 50 ml of methylene chloride each time
  4. washThe organic phases were washed once with 50 ml of water, twice with 30 ml of 5% aqueous acetic acid each time
  5. dry with materialtwice with 30 ml of water each time, dried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-723eac23960640cb82332e69264bfe48
Source dataset
uspto-grants-1985_07
Patent number
US04528114

Reaction notes

Loading…