Dicyclohexylcarbodiimide → HCID 86758292, compound

HRID 2227109Notes

Reaction equation

HRID 2227109 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[OH:22])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:23][C:24](C)=[CH:25][CH2:26][CH2:27][CH:28]1[CH2:33][CH2:32][C:31]([C:34](O)=[O:35])=[CH:30][CH2:29]1.C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>O.O1CCCC1>[CH2:27]([CH:28]1[CH2:33][CH2:32][C:31]([C:34]([O:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][CH2:14][CH2:13][CH2:12][CH:9]2[CH2:8][CH2:7][CH:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]2)=[O:35])=[CH:30][CH2:29]1)[CH2:26][CH2:25][CH2:24][CH3:23]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 18471825HCID 18471825, compoundHCID 178444440HCID 178444440, compound

Product 1

HCID 86758292HCID 86758292, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a round-bottom flask equipped with a stirbar is added phenol 3H (R=pentyl) (5 g), (4-(4-Methyl-3-pentenyl)-1-cyclohexenyl)carboxylic acid (R=n-pentyl) (3.3 g), dicyclohexylcarbodiimide (5.11 g), dimethylaminopyridine (202 mg), and anhydrous tetrahydrofuran (50 mL). The reaction is stirred overnight, at which time the solution is poured into water and extracted with 1:1 hexanes:ethyl acetate. The combined organic layers are washed with brine and dried over potassium carbonate, and the solution is concentrated in vacuo. Filtration through silica gel using 10% ethyl acetate in hexanes gives the pure product.

Workup

  1. customTo a round-bottom flask equipped with a stirbar
  2. extractionextracted with 1:1 hexanes
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over potassium carbonate
  5. concentrationthe solution is concentrated in vacuo
  6. filtrationFiltration through silica gel using 10% ethyl acetate in hexanes
  7. customgives the pure product

Sources & evidence

ORD record
ord-052919a58443459794b1083aada7652c
Source dataset
uspto-grants-2002_07
Patent number
US06413448B1

Reaction notes

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