Pivalic acid → HCID 178448054, compound

HRID 1590518Notes

Reaction equation

HRID 1590518 reaction equation
[C:1]([OH:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH:8](/[C@H:11]1[CH2:16][CH2:15][C@H:14]([C@H:17]2[CH2:22][CH2:21][C@H:20](/[CH:23]=[CH:24]/[CH2:25]O)[CH2:19][CH2:18]2)[CH2:13][CH2:12]1)=[CH:9]\[CH3:10]>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([O:7][CH2:25]/[CH:24]=[CH:23]/[C@H:20]1[CH2:21][CH2:22][C@H:17]([C@H:14]2[CH2:13][CH2:12][C@H:11](/[CH:8]=[CH:9]/[CH3:10])[CH2:16][CH2:15]2)[CH2:18][CH2:19]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 6417Pivalic acidHCID 178448050HCID 178448050, compound

Product 1

HCID 178448054HCID 178448054, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.4 g of pivalic acid, 1.0 g of 3E-[trans-4-(trans-4-[1E-propenyl]cyclohexyl)cyclohexyl]allyl alcohol and 0.1 g of 4-(dimethylamino)pyridine were dissolved in 50 ml of dichloromethane and the solution was treated portionwise within 10 minutes while stirring with 0.9 g of N,N'-dicyclohexylcarodiimide. The mixture was stirred at room temperature overnight and then filtered. The filtrate was diluted with dichloromethane, washed twice with 50 ml of saturated sodium carbonate solution each time and then with water, dried over magnesium sulphate, filtered and then concentrated. Chromatography of the residue on silica gel with toluene gave 1.3 g of 3E-[trans-4-(trans-4-[1E-propenyl]cyclohexyl)cyclohexyl]-allyl pivalate.

Workup

  1. additionthe solution was treated portionwise within 10 minutes
  2. stirringThe mixture was stirred at room temperature overnight
  3. filtrationfiltered
  4. additionThe filtrate was diluted with dichloromethane
  5. washwashed twice with 50 ml of saturated sodium carbonate solution each time
  6. dry with materialwith water, dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f91edb5eace4454d80a88435630e6d80
Source dataset
uspto-grants-1993_04
Patent number
US05204018

Reaction notes

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