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

HRID 1082008

反応式

HRID 1082008 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-584dbaf440554a1dbd7883095777b69f
出典データセット
uspto-grants-1996_12
特許番号
US05587504

関連ノート

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