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2-Methylbutanoic Acid → (s)-5-n-Undecyloxy-2-[4-(2-methylbutanoyloxy)phenyl]pyrimidine

HRID 4455
Notes
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Reaction equation

HRID 4455 reaction equation
[CH3:1][CH:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].[CH2:8]([O:19][C:20]1[CH:21]=[N:22][C:23]([C:26]2[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=2)=[N:24][CH:25]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH2:8]([O:19][C:20]1[CH:25]=[N:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([O:4][C:3](=[O:5])[C@@H:2]([CH3:1])[CH2:6][CH3:7])=[CH:28][CH:27]=2)=[N:22][CH:21]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 83142-Methylbutanoic AcidHCID 1357361844-[5-(Undecyloxy)pyrimidin-2(1H)-ylidene]cyclohexa-2,5-dien-1-one

Product 1

HCID 18611672(s)-5-n-Undecyloxy-2-[4-(2-methylbutanoyloxy)phenyl]pyrimidineYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212Chloroform
Solvent

Procedure

Pour 0.328 g of 2-methylbutanoic acid synthesized from (s)-amylalcohol ([α]D23 -5.8° (neat)), 1.1 g of 4-(5-n-undecyloxy-2-pyrimidinyl)phenol, 8 ml of anhydrous chloroform and 0.662 g of 4-dimethylaminopyridine, S,S'-dicyclohexylcarbodimide into a 25 ml flask and allow to react for one whole day at room temperature. After the reaction, filter and separate the insoluble matters, and extract the reaction product with chloroform. The organic layer is washed with water, 2N hydrochloric acid and water, dried and evaporated to remove the organic solvent. The reaction product is purified with silica gel chromatography and re-crystallized crystal, and then optically active (s)-5-n-undecyloxy-2-[4-(2-methylbutanoyloxy)phenyl]pyrimidine is obtained at a yield of 70%.

Workup

  1. customto react for one whole day at room temperature
  2. customAfter the reaction
  3. filtrationfilter
  4. customseparate the insoluble matters
  5. extractionextract the reaction product with chloroform
  6. washThe organic layer is washed with water, 2N hydrochloric acid and water
  7. customdried
  8. customevaporated
  9. customto remove the organic solvent
  10. customThe reaction product is purified with silica gel chromatography
  11. customre-crystallized crystal

Sources & evidence

ORD record
ord-0f56b0f450a745bdbb47e42936a87fa7
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04725688

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes