Hydrochloric Acid → HCID 18471818, compound

HRID 326957Notes

Reaction equation

HRID 326957 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]([C:16]1[CH:17]=[N:18][C:19]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[N:20][CH:21]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].Cl>C(N(CC)CC)C>[CH2:7]([C:6]1[CH2:16][CH2:21][CH:4]([C:5]([O:28][C:25]2[CH:24]=[CH:23][C:22]([C:19]3[N:20]=[CH:21][C:16]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:17][N:18]=3)=[CH:27][CH:26]=2)=[O:1])[CH2:3][CH:2]=1)[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 135585902Phenol, 4-(5-decyl-2-pyrimidinyl)-

Product 1

HCID 18471818HCID 18471818, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2-{4'-[(4-pentyl-3-cyclohexenyl)-carbonyloxy]-phenyl}-5-decylpyrimidine is synthesized as follows. Tetrahydrofuran (35 carboxyl chloride (2.3 g) and 5-decyl-2-(4'-hydroxyphenyl)-pyrimidine (3.66 g). The reaction mixture is stirred until homogenous, then triethylamine (2.5 ml) is added. The reaction mixture immediately turns turbid. The turbid solution is stirred 1 hour, poured into a dilute (5%) hydrochloric acid solution, and extracted with ethyl acetate. The combined organic layers are then extracted with saturated sodium chloride, dried over sodium sulfate, and the solvent removed in vacuo. The product is purified by flash chromatography using 10% ethyl acetate in hexane as the eluent, and recrystallized from acetonitrile to produce the product, 2-{4'-[(4-pentyl-3-cyclohexenyl)-carbonyloxy]-phenyl)-5-decylpyrimidine.

Workup

  1. custom2-{4'-[(4-pentyl-3-cyclohexenyl)-carbonyloxy]-phenyl}-5-decylpyrimidine is synthesized
  2. additionis added
  3. additionpoured into
  4. extractionextracted with ethyl acetate
  5. extractionThe combined organic layers are then extracted with saturated sodium chloride
  6. dry with materialdried over sodium sulfate
  7. customthe solvent removed in vacuo
  8. customThe product is purified by flash chromatography
  9. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-7ac6c862cb624160aec159079ef5a7cd
Source dataset
uspto-grants-1993_12
Patent number
US05271864

Reaction notes

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