HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Dicyclohexylcarbodiimide → Benzyl 6-(3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carbonyloxy)-nicotinate

HRID 1633
Notes
Print preview

Reaction equation

HRID 1633 reaction equation
[CH2:1]([C:7]1[C:8]([C:21]([OH:23])=[O:22])=[CH:9][C:10]2[C:11]([CH3:20])([CH3:19])[CH2:12][CH2:13][C:14]([CH3:18])([CH3:17])[C:15]=2[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O[C:25]1[CH:40]=[CH:39][C:28]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])=[CH:27][N:26]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([C:7]1[C:8]([C:21]([O:23][C:25]2[CH:40]=[CH:39][C:28]([C:29]([O:31][CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:30])=[CH:27][N:26]=2)=[O:22])=[CH:9][C:10]2[C:11]([CH3:20])([CH3:19])[CH2:12][CH2:13][C:14]([CH3:17])([CH3:18])[C:15]=2[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 110125513-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carboxylic acidHCID 178418417HCID 178418417, compound

Product 1

HCID 10973423Benzyl 6-(3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carbonyloxy)-nicotinateYield 57%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

6 g of 3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carboxylic acid were dissolved in 180 ml of methylene chloride. After the addition of a solution of 4.8 g of benzyl 6-hydroxy-nicotinate in 160 ml of methylene chloride and of 2.3 g of 4-dimethylaminopyridine, the solution was cooled to 0° C. and treated with 4.4 g of dicyclohexylcarbodiimide. The reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 2 hours, thereafter poured into ice-cold aqueous ammonium chloride solution, extracted several times with ether, washed with water, dried over sodium sulfate and evaporated. The crude product, for the most part crystalline, was filtered over silica gel (eluent hexane/ethyl acetate=9:1) and recrystallized from hexane. After repeated crystallization of the mother liquor there were obtained all together 5.7 g of benzyl 6-(3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carbonyloxy)-nicotinate in colorless crystals, m.p. 94°-95° C.

Workup

  1. additionpoured into ice-cold aqueous ammonium chloride solution
  2. extractionextracted several times with ether
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. filtrationThe crude product, for the most part crystalline, was filtered over silica gel (eluent hexane/ethyl acetate=9:1)
  7. customrecrystallized from hexane
  8. customcrystallization of the mother liquor

Sources & evidence

ORD record
ord-c4710f63ab8144a9acdfc1350b467c98
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05726191

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes