Ethanol → 2-(4-(1-Hydroxyethyl)phenyl)-5-decyloxypyrimidine

HRID 1160

Reaction equation

HRID 1160 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:12][N:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(O)C.C(Cl)(Cl)Cl.[BH4-].[Na+]>O>[OH:3][CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:12][N:11]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 196949012-(4-Acetylphenyl)-5-decyloxypyrimidine

Product 1

HCID 214682802-(4-(1-Hydroxyethyl)phenyl)-5-decyloxypyrimidineYield 100.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

35.5 g (0.1 mo1) of 2-(4-acetylphenyl)-5-decyloxypyrimidine, 300 ml of ethanol and 300 ml of chloroform were supplied into a four-necked flask equipped with a stirrer and a thermometer. Then 2.8 g (0.075 mol) of sodium borohydride was added at 30°-40° C. and the mixture was stirred at the same temperature for 4 hours. The resulting reaction mixture was poured into 500 ml of water, followed by extraction and liquid separation, and the obtained chloroform layer was washed with water, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 35.8 g of 2-(4-(1-hydroxyethyl) phenyl)-5-decyloxypyrimidine (II-c-11) (yield: 100%).

Workup

  1. customequipped with a stirrer
  2. customThe resulting reaction mixture
  3. extractionfollowed by extraction and liquid separation
  4. washthe obtained chloroform layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8266c5cd4a68414b8c3137da7bc01eef
Source dataset
uspto-grants-1998_03
Patent number
US05723610

Linked notes

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