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

HRID 1929406Notes

Reaction equation

HRID 1929406 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 triphenylphosphine (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-7bf738318fe74cfb8ab5524277e69bf3
Source dataset
uspto-grants-2012_05
Patent number
US08188077B2

Reaction notes

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