1,1-Dibromoethane → 4,4-Dimethyl-2-(4'-tetrahydropyranyloxymethylbiphenyl-2-yl)oxazoline

HRID 743748

Reaction equation

HRID 743748 reaction equation
[Mg].BrC(Br)C.BrC1C=CC(C[C:12]2([O:18][C:19]3([CH2:25][C:26]4[CH:31]=[CH:30][C:29](Br)=[CH:28]C=4)CCCCO3)[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=CC=1.[CH3:35][C:36]1([CH3:49])[CH2:40][O:39][C:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2OC)=[N:37]1.[Cl-].[NH4+]>O1CCCC1>[CH3:49][C:36]1([CH3:35])[CH2:40][O:39][C:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[C:30]2[CH:31]=[CH:26][C:25]([CH2:19][O:18][CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)=[CH:28][CH:29]=2)=[N:37]1

Participants

7

Reactant 5

HCID 112011,1-DibromoethaneHCID 25517Ammonium ChlorideHCID 3331894,4-Dimethyl-2-(2-methoxyphenyl)oxazolineHCID 5462224Magnesium2×HCID 699599014-Bromobenzyl-tetrahydropyranyl ether

Product 1

HCID 153808764,4-Dimethyl-2-(4'-tetrahydropyranyloxymethylbiphenyl-2-yl)oxazolineYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Tetrahydrofuran (15 ml) was added to 1.2 g (49.4 mmol) of flaky magnesium, followed by the addition of a small amount of dibromoethane under stirring. After the confirmation of bubbling, a solution of 11.0 g (40.6 mmol) of 4-bromobenzyl-tetrahydropyranyl ether in tetrahydrofuran (15 ml) was dropwise added thereto. After the confirmation of the dissolution of the magnesium, the resulting mixture was further stirred at room temperature for one hour. Then, a solution of 7.0 g (34.1 mmol) of 4,4-dimethyl-2-(2'-methoxyphenyl)oxazoline in tetrahydrofuran (5 ml) was dropwise added thereto, followed by stirring for 12 hours. The reaction liquid was poured into a saturated aqueous solution of ammonium chloride, followed by the extraction with chloroform. After washing with water and drying, vacuum concentration was conducted. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 6.61 g of the title compound as an oil (yield 53%).

Workup

  1. customAfter the confirmation of bubbling
  2. stirringthe resulting mixture was further stirred at room temperature for one hour
  3. stirringby stirring for 12 hours
  4. customThe reaction liquid
  5. extractionfollowed by the extraction with chloroform
  6. washAfter washing with water
  7. customdrying
  8. concentrationvacuum concentration
  9. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-ed78e7536d664d8aa567a2be4872be4f
Source dataset
uspto-grants-1996_09
Patent number
US05557002

Linked notes

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