Diethyl Ether → (4-Butylidene-1-phenyl-cyclohexyl)-dimethylamine

HRID 76921

反応式

HRID 76921 の反応式
CCOCC.[CH3:6][N:7]([CH3:21])[C:8]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1.[CH2:22]1[CH2:26]O[CH2:24][CH2:23]1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC>[CH:26](=[C:11]1[CH2:12][CH2:13][C:8]([N:7]([CH3:21])[CH3:6])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9][CH2:10]1)[CH2:22][CH2:23][CH3:24]

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

生成物 1

HCID 68632980(4-Butylidene-1-phenyl-cyclohexyl)-dimethylamine

試薬・触媒・溶媒 1

HCID 159628Butyltriphenylphosphonium bromide触媒

実験手順

Potassium tert-butylate (2.75 g, 23.7 mmol) was provided in abs. ether (50 mL) in argon and mixed with butyl-triphenyl phosphonium bromide (9.45 g, 23.7 mmol). The batch was heated for 30 min to 40° C. 4-dimethylamino-4-phenyl cyclohexanone (5.00 g, 23.0 mmol) dissolved in abs. THF (50 mL) was then added carefully in drops (exothermic reaction). The batch was heated for 6.5 h to 50° C. and stirred overnight at room temperature. The batch was then concentrated in a vacuum until dry, taken up in dioxan (20 mL) and mixed with HCl/dioxan (5 mL). A precipitate separated out during this. This was filtered off, washed with ether (10 mL), then basified with 2N NaOH and extracted with dichloromethane (2×40 mL). The organic phase was dried over Na2SO4, filtered and concentrated in a vacuum until dry.

後処理

  1. temperatureThe batch was heated for 30 min to 40° C
  2. temperatureThe batch was heated for 6.5 h to 50° C.
  3. concentrationThe batch was then concentrated in a vacuum
  4. customuntil dry
  5. additionmixed with HCl/dioxan (5 mL)
  6. customA precipitate separated out during this
  7. filtrationThis was filtered off
  8. washwashed with ether (10 mL)
  9. extractionextracted with dichloromethane (2×40 mL)
  10. dry with materialThe organic phase was dried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in a vacuum
  13. customuntil dry

出典と根拠

ORDレコード
ord-fe2b2fc9c85a469fbf94e00b697aa1df
出典データセット
uspto-grants-2014_09
特許番号
US08835689B2

関連ノート

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