Cyclohexanone → Spiro(5.5)undecan-1-one

HRID 2070580

反応式

HRID 2070580 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 573924Spiro(5.5)undecan-1-one収率 65.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8308357151d441059f21afd1306cb7f6
出典データセット
uspto-grants-2012_10
特許番号
US08299296B2

関連ノート

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