Hydrochloric Acid → Spiro(5.5)undecan-1-one

HRID 12046

反応式

HRID 12046 の反応式
Br[C:2](Br)([CH2:5][CH3:6])[CH2:3][CH3:4].[C:8]1(=[O:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[K].C([O-])(C)(C)C.Cl>C1(C)C=CC=CC=1>[C:8]1(=[O:14])[C:13]2([CH2:6][CH2:5][CH2:2][CH2:3][CH2:4]2)[CH2:12][CH2:11][CH2:10][CH2:9]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 135557303,3-DibromopentaneHCID 50987170Potassium tertbutoxide

生成物 1

HCID 573924Spiro(5.5)undecan-1-one

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Dibromopentane (5 mmol) is added to a solution of cyclohexanone (5 mmol) and potassium-tert-butanolate (10 mmol) in toluene (7.5 ml) and the reaction mixture is refluxed for 48 hours. After cooling to room temperature 25% hydrochloric acid is added and extraction is carried out with diethyl ether. The combined organic phases produce, after drying over sodium sulphate, removal of the solvent in a vacuum and chromatography of the residue using silica gel (ethyl acetate/heptane, 1:5) pure spiro[5.5]undecan-1-one (Tetrahedron 1964, 20, 2553-2573): tR 1.90 min. (LC-2); ESI-MS (+): m/z 167.27 [M+H]+.

後処理

  1. temperaturethe reaction mixture is refluxed for 48 hours
  2. additionis added
  3. extractionextraction
  4. customThe combined organic phases produce
  5. dry with materialafter drying over sodium sulphate, removal of the solvent in a vacuum and chromatography of the residue

出典と根拠

ORDレコード
ord-dc56b055e1544a4a8c8c799f73e8849d
出典データセット
uspto-grants-2010_06
特許番号
US07727979B2

関連ノート

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