Pyridine → 4-(3-Methyl-5-phenyl-pentyloxycarbonyloxy)-undecanoic acid 2-naphthalen-2-yl-2-oxo-ethyl ester

HRID 1384415Notes

Reaction equation

HRID 1384415 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=[O:27])[CH2:12][O:13][C:14](=[O:26])[CH2:15][CH2:16][CH:17]([OH:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].N1C=CC=CC=1.[CH3:34][CH:35]([CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:36][CH2:37][OH:38].Cl[C:48]([O-])=[O:49]>C1COCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=[O:27])[CH2:12][O:13][C:14](=[O:26])[CH2:15][CH2:16][CH:17]([O:25][C:48]([O:38][CH2:37][CH2:36][CH:35]([CH3:34])[CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:49])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 211868244-Hydroxy-undecanoic acid-2-naphthalen-2-yl-2-oxo-ethyl esterHCID 867571413-Methyl-5-phenyl-pentanol chloroformate

Product 1

HCID 541043384-(3-Methyl-5-phenyl-pentyloxycarbonyloxy)-undecanoic acid 2-naphthalen-2-yl-2-oxo-ethyl esterYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4.00 g of 4-hydroxy-undecanoic acid-2-naphthalen-2-yl-2-oxo-ethyl ester and 1.71 g of pyridine in 20 ml of THF, a solution of 2.91 g of 3-methyl-5-phenyl-pentanol-chloroformate in 10 ml of THF was dropped in at 0° C. The mixture was stirred for 3 hours at room temperature. Then, the reaction mixture was quenched with water and extracted with ether. The organic phase was washed with 2N HCl, saturated sodium bicarbonate, and water. Then, the mixture was dried, filtered, and evaporated to dryness. The resulting yellow oil was purified by chromatography to yield 5.46 g of a colorless oil.

Workup

  1. customThen, the reaction mixture was quenched with water
  2. extractionextracted with ether
  3. washThe organic phase was washed with 2N HCl, saturated sodium bicarbonate, and water
  4. customThen, the mixture was dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe resulting yellow oil was purified by chromatography

Sources & evidence

ORD record
ord-d7e18d01bfdf4e978b73d821399304bc
Source dataset
uspto-grants-2001_07
Patent number
US06258854B1

Reaction notes

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