Dicyclohexylcarbodiimide → HCID 67200982, compound

HRID 544814Notes

Reaction equation

HRID 544814 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[CH:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)=[CH2:17].O[CH:28]([CH3:41])[CH2:29][C:30]([CH:32]1[C:37]([CH3:39])([CH3:38])[CH2:36][CH:35]=[CH:34][CH:33]1[CH3:40])=[O:31]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([O:24][CH:28]([CH3:41])[CH2:29][C:30](=[O:31])[CH:32]2[C:37]([CH3:39])([CH3:38])[CH2:36][CH:35]=[CH:34][CH:33]2[CH3:40])=[O:23])=[CH:20][CH:19]=1)=[CH2:17]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 140984-Vinylbenzoic acidHCID 67200945HCID 67200945, compound

Product 1

HCID 67200982HCID 67200982, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of DCC (3.60 g, 17.5 mmol) in 10 ml of CH2Cl2 was added to an ice-cold solution of 4-vinylbenzoic acid (2.35 g, 15.9 mmol), DMAP (1.55 g, 12.7 mmol) and 3-hydroxy-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone (4.00 g, 19.1 mmol) in 30 ml of CH2Cl2. The reaction mixture was stirred at room temperature for 5 days. The precipitate was filtered off and the filtrate taken up in CH2Cl2, washed twice with 10% aqueous HCl, saturated aqueous Na2CO3 and saturated aqueous NaCl. The organic phases were dried over Na2SO4 and concentrated. Flash-chromatography over SiO2 (heptane/ether 9:1) gave 4.02 g of the desired compound (yield: 74%).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed twice with 10% aqueous HCl, saturated aqueous Na2CO3 and saturated aqueous NaCl
  3. dry with materialThe organic phases were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-72dec71ed36a4d23a0be103cbf81a9ac
Source dataset
uspto-grants-2011_05
Patent number
US07935669B2

Reaction notes

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