Iodine → 3-Methyl-8-(tetrahydropyran-2-yloxy)octanoic acid sec-butyl ester

HRID 127805ノート

反応式

HRID 127805 の反応式
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1.C(Br)C.II.[CH:20]([O:24][C:25](=[O:29])/[CH:26]=[CH:27]/[CH3:28])([CH2:22][CH3:23])[CH3:21].[Cl-].[NH4+]>O1CCCC1>[CH:20]([O:24][C:25](=[O:29])[CH2:26][CH:27]([CH3:28])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1)([CH2:22][CH3:23])[CH3:21]

参加物

8

反応物 6

HCID 807IodineHCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 27869332-(5-Bromopentyloxy)tetrahydro-2H-pyranHCID 5366041sec-Butyl CrotonateHCID 5462224Magnesium

生成物 1

HCID 543107583-Methyl-8-(tetrahydropyran-2-yloxy)octanoic acid sec-butyl ester収率 46.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Under an atmosphere of nitrogen, a mixture of 250 mg of magnesium, 2.8 g of 5-bromo-1-(tetrahydropyran-2-yloxy)pentane, 200 μl of ethyl bromide, a trace amount of iodine and 4 ml of tetrahydrofuran was refluxed with heating for one hour. To it were added 516 mg of crotonic acid sec-butyl ester and 14 mg of cuprous chloride at 0° C. over a period of 30 minutes, the mixture stirred at 0° C. for 15 minutes, and then at room temperature for one hour. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate, the extract washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of methylene chloride and ethyl acetate (20:1) as eluent to give 529 mg of the subtitle compound having the following physical characteristics:

後処理

  1. temperaturewith heating for one hour
  2. waitat room temperature for one hour
  3. extractionextracted with ethyl acetate
  4. washthe extract washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel using
  8. additiona mixture of methylene chloride and ethyl acetate (20:1) as eluent

出典と根拠

ORDレコード
ord-8eab4adeecbe43f0b1aa23987f6975db
出典データセット
uspto-grants-1981_03
特許番号
US04256757

反応ノート

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