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Tetrahydrofuran → 1-Benzoyloxy-3-hydroxymethyl-2-methylenecyclobutane

HRID 5958
ノート
印刷プレビュー

反応式

HRID 5958 の反応式
[C:1]([O:9][CH:10]1[CH2:13][CH:12]([CH2:14][OH:15])[CH:11]1[CH2:16]Br)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>C(Cl)Cl>[C:1]([O:9][CH:10]1[CH2:13][CH:12]([CH2:14][OH:15])[C:11]1=[CH2:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 197942491-Benzoyloxy-2-bromomethyl-3-hydroxymethylcyclobutane

生成物 1

HCID 197943161-Benzoyloxy-3-hydroxymethyl-2-methylenecyclobutane収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1-Benzoyloxy-2-bromomethyl-3-hydroxymethylcyclobutane (2.5 g, 8.36 mmol) from Step F and tetra-n-butylammonium fluoride ((8.1 g, 25 mmol) were combined in 200 mL of freshly distilled THF and the reaction mixture was stirred at ambient temperature, under a nitrogen atmosphere, overnight. The volume of the reaction mixture was then reduced to 25 mL and this was dissolved in 250 mL of methylene chloride. The methylene chloride solution was washed with 150 mL of water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue (4.9 g) was dissolved in ~5 mL of methylene chloride and purified on a 2.5×35 cm silica gel column eluted @ 5 psi with a step-wise (4×200 mL steps) of methanol in methylene chloride from 0% to 3% methanol to give 1.54 g (85% yield) of the title compound as a syrup; 1H NMR (CDCl3) δ 2.38 (m, 2H), 3.22 (m, 1H), 3.69-3.85 (m, 2H), 5.13 (t, 1H), 5.32 (t, 1H), 5.79 (M, 1H), 7.45 (m, 2H), 7.58 (m, 1H), 8.08 (m, 2H); MS DCI-NH3M/Z: 219 (M+H)+, 236 (M+NH4)+.

後処理

  1. washThe methylene chloride solution was washed with 150 mL of water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue (4.9 g) was dissolved in ~5 mL of methylene chloride
  6. custompurified on a 2.5×35 cm silica gel column
  7. washeluted @ 5 psi with a step-wise (4×200 mL steps) of methanol in methylene chloride from 0% to 3% methanol

出典と根拠

ORDレコード
ord-3d62ca5f75db401fa27c51497eb470a9
出典データセット
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05246931

反応ノート

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