Ethylparaben → 4-(2-Adamantan-1-yl-ethoxy)-benzoic acid ethyl ester

HRID 1798438Notes

Reaction equation

HRID 1798438 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[C:13]12([CH2:23][CH2:24]O)[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCCC1>[CH2:9]([O:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:24][CH2:23][C:13]23[CH2:22][CH:17]4[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]4)[CH2:14]2)[CH2:20]3)=[CH:12][CH:11]=1)[CH3:10]

Participants

6

Reactant 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 1108102-(Tricyclo(3.3.1.1'3,7)dec-1-yl)ethanol

Product 1

HCID 574749894-(2-Adamantan-1-yl-ethoxy)-benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-hydroxybenzoate (83 mg) and 1-adamantaneethanol (90 mg) were combined in tetrahydrofuran (2 mL). Polymer-supported triphenylphospine (250 mg of 3 mmol/g) and di-tert-butyl azodicarboxylate (173 mg) were added. The reaction was stirred at room temperature overnight. The resin was removed by filtration through celite. The filtrate was concentrated under vacuum, and the residue was triturated with 95/5 hexanes/ether to afford the title compound.

Workup

  1. customThe resin was removed by filtration through celite
  2. concentrationThe filtrate was concentrated under vacuum
  3. customthe residue was triturated with 95/5 hexanes/ether

Sources & evidence

ORD record
ord-5efb7f7081014632be0b9f02dfe96747
Source dataset
uspto-grants-2013_01
Patent number
US08343967B2

Reaction notes

Loading…