Sodium Fluoride → 2-Ethenylphenol

HRID 893513

反応式

HRID 893513 の反応式
[O:1]([C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[CH2:12])[Si](C(C)(C)C)(C)C.BrN1C(=O)CCC1=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F-].[F-].[K+].[F-].[Na+].[F-].[F-].[Ca+2]>O1CCCC1.Cl(O)(=O)(=O)=O.C(OCC)C>[CH:11]([C:10]1[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=1[OH:1])=[CH2:12]

参加物

11

反応物 7

HCID 5235Sodium FluorideHCID 28179Fluoride IonHCID 67184N-bromobutanimideHCID 84512Calcium FluorideHCID 522689Potassium FluorideHCID 2724141Tetrabutylammonium FluorideHCID 221864152-t-Butyldimethylsiloxy styrene

生成物 1

HCID 1354422-Ethenylphenol

試薬・触媒・溶媒 3

HCID 24247Perchloric Acid触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2-ethenyl phenol was synthesized according to the procedure of Corson et al. (J. Org. Chem., 1958, 23, 544) and silated by standard procedures. 2-t-butyldimethylsiloxy styrene (550 mg, 2.03 mmoles) was dissolved in tetrahydrofuran (4.0 mL). Exo-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane-2-ol (690 mg, 4.06 mmoles) and N-bromosuccinimide were added. One drop of perchloric acid (70%) was added. The reaction was stirred for 11/2 hrs after which time a 1M solution of tetrabutylammonium fluoride in THF (2.5 mL) (any fluoride source, such as KF, NaF, CaF2, HF will suffice) was added and the solution was stirred for an hour. The reaction mixture was diluted with diethyl ether and washed with H2O. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated. It was then chromatographed on SiO2 (10-20% Et2O/hexane) to obtain 210 mg of the desired product in about 95% purity.

後処理

  1. additionwas added
  2. washwashed with H2O
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customIt was then chromatographed on SiO2 (10-20% Et2O/hexane)

出典と根拠

ORDレコード
ord-b5f6e5687cef4b8a9e1f09bc60336dd9
出典データセット
uspto-grants-1992_06
特許番号
US05125954

関連ノート

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