Water → HCID 14720911、化合物

HRID 2073476ノート

反応式

HRID 2073476 の反応式
[Cl:1][CH:2]1[CH2:5][CH:4]([CH2:6][OH:7])[CH2:3]1.[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[H-].[Na+].O>CN(C)C=O>[Cl:1][CH:2]1[CH2:5][CH:4]([CH2:6][O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1

参加物

6

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 13813819(3-Chlorocyclobutyl)methanol

生成物 1

HCID 14720911HCID 14720911、化合物収率 94.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3-chlorocyclobutanemethanol (17.3 g, 0.143 mole) and benzylbromide (26.96 g, 0.158 mole) in dry dimethylformamide (123 ml) was stirred at room temperature under an argon atmosphere and a 60% suspension of sodium hydride (6.31 g 0.158 g mole) was added. The reaction was stirred at ambient temperature for 22.5 hours. The reaction mixture was poured into 600 ml of water and the aqueous mixture extracted with ethyl acetate (4×500 ml). The ethyl acetate extracts were combined and dried over anhydrous sodium sulfate and the ethyl acetate evaporated in vacuo yielding the crude product as a yellow oil. The material was purified on a 2-liter Merck silica gel column eluting with 3 liters of hexane, followed by 5% ethyl acetate/hexane. The fractions containing the desired product were combined and the volatiles evaporated in vacuo yielding 28.6 g of the title compound as a pale yellow oil.

後処理

  1. stirringThe reaction was stirred at ambient temperature for 22.5 hours
  2. extractionthe aqueous mixture extracted with ethyl acetate (4×500 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe ethyl acetate evaporated in vacuo
  5. customyielding the crude product as a yellow oil
  6. customThe material was purified on a 2-liter Merck silica gel column
  7. washeluting with 3 liters of hexane
  8. additionThe fractions containing the desired product
  9. customthe volatiles evaporated in vacuo

出典と根拠

ORDレコード
ord-f3238f73d2f04f0baa996c6989b60f6c
出典データセット
uspto-grants-1990_04
特許番号
US04918075

反応ノート

読み込み中…