Cyclohexanone → Spiro(5.5)undecan-1-one

HRID 2070580

반응식

HRID 2070580 반응식
CC(C)([O-])C.[K+].[C:7]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br>C1(C)C=CC=CC=1>[C:7]1(=[O:13])[C:12]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:11][CH2:10][CH2:9][CH2:8]1

참가 물질

5

반응물 3

HCID 7967CyclohexanoneHCID 81001,5-DibromopentaneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 573924Spiro(5.5)undecan-1-one수율 65.6%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

To a suspension of potassium tert-butoxide (24.4 g) in toluene (100 mL) was added a solution of cyclohexanone (10.67 g) and 1,5-dibromopentane (25 g) in toluene (50 mL) while stirring. The mixture was stirred at 100° C. for 4 hours. After cooling down to room temperature, the resulting solid was filtered and washed with toluene. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:15) to give spiro[5.5]undecan-1-one (11.85 g).

후처리

  1. stirringThe mixture was stirred at 100° C. for 4 hours
  2. filtrationthe resulting solid was filtered
  3. washwashed with toluene
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:15)

출처 및 근거

ORD 기록
ord-8308357151d441059f21afd1306cb7f6
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299296B2

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