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

HRID 12046

반응식

HRID 12046 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 573924Spiro(5.5)undecan-1-one

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-dc56b055e1544a4a8c8c799f73e8849d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727979B2

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