Triphenylphosphine → 4-(5-Undecyl-pyrimidin-2-yl)phenyl (3-ethyl-cyclopentan-1-yl)methyl ether

HRID 1826556Notes

Reaction equation

HRID 1826556 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:32]([C:43]1[CH:44]=[N:45][C:46]([C:49]2[CH:54]=[CH:53][C:52]([OH:55])=[CH:51][CH:50]=2)=[N:47][CH:48]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].[CH2:56]([CH:58]1[CH2:62][CH2:61][CH:60]([CH2:63]O)[CH2:59]1)[CH3:57]>C1COCC1>[CH2:56]([CH:58]1[CH2:62][CH2:61][CH:60]([CH2:63][O:55][C:52]2[CH:51]=[CH:50][C:49]([C:46]3[N:47]=[CH:48][C:43]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[CH:44][N:45]=3)=[CH:54][CH:53]=2)[CH2:59]1)[CH3:57]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22134208(3-Ethylcyclopentyl)methanolHCID 1356196824-(5-Undecylpyrimidin-2-yl)phenol

Product 1

HCID 701128834-(5-Undecyl-pyrimidin-2-yl)phenyl (3-ethyl-cyclopentan-1-yl)methyl ether

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A fully reacted mixture of equimolar amounts of diethyl azodicarboxylate and triphenylphosphine in THF is admixed with equimolar amounts of 4-(5-undecyl-pyrimidin-2-yl)phenol and 3-ethyl-cyclopentan-1-yl-methanol (prepared by LiAlH4 reduction of methyl 3-ethyl-cyclopentanecarboxylic acid). The mixture is stirred for 24 h at room temperature and then evaporated to dryness under reduced pressure. Purification by chromatography (silica gel, dichloromethane) and recrystallization affords the target compound.

Workup

  1. customevaporated to dryness under reduced pressure
  2. customPurification
  3. customby chromatography (silica gel, dichloromethane) and recrystallization
  4. customaffords the target compound

Sources & evidence

ORD record
ord-b069b6d95c594dc887798e2bfe81c520
Source dataset
uspto-grants-2006_05
Patent number
US07052742B1

Reaction notes

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