Oxygen → 3-(3-Bromophenyl)oxetane

HRID 1475788ノート

反応式

HRID 1475788 の反応式
[Br:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl.N[C@@H]1CC[CH2:26][CH2:25][C@H:24]1[OH:29].O=O>CC(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:25]2[CH2:24][O:29][CH2:26]2)[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 977OxygenHCID 2724254Sodium bis(trimethylsilyl)amideHCID 2734318(3-Bromophenyl)boronic acidHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-

生成物 1

HCID 534843193-(3-Bromophenyl)oxetane収率 939.9%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

4.7 g of 3-bromophenylboronic acid, 219 mg of NiI2, 4.3 g of sodium bis(trimethylsilyl)amide, and 106 mg of trans-2-aminocyclohexanol hydrochloride were added to 14 ml of anhydrous 2-propanol and oxygen removed by passing argon through the mixture for 10 minutes. Then, a solution of 2.2 g of 3-iodo-oxetane in 1 ml of anhydrous 2-propanol was added and the mixture kept at 80° C. under microwave irradiation for 50 minutes. The mixture was then evaporated, distributed between 100 ml of water and 100 ml of EA, and the aqueous layer extracted twice using 20 ml of EA each. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP 1:4 yielded 1.4 g of the title compound, colorless oil. Rf (EA/HEP 1:4)=0.27

後処理

  1. customremoved
  2. customfor 10 minutes
  3. additionThen, a solution of 2.2 g of 3-iodo-oxetane in 1 ml of anhydrous 2-propanol was added
  4. customthe mixture kept at 80° C. under microwave irradiation for 50 minutes
  5. customThe mixture was then evaporated
  6. extractionthe aqueous layer extracted twice
  7. customThe organic layer was then dried
  8. customevaporated

出典と根拠

ORDレコード
ord-4a7d303081354234a32e3084b38c6142
出典データセット
uspto-grants-2015_04
特許番号
US09018383B2

反応ノート

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