Sodium Bicarbonate → (4-Methoxymethylene-cyclohexyl)-methyl-carbamic acid benzyl ester

HRID 25655ノート

反応式

HRID 25655 の反応式
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH2:30]([O:37][C:38](=[O:48])[N:39]([CH3:47])[CH:40]1[CH2:45][CH2:44][C:43](=O)[CH2:42][CH2:41]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:30]([O:37][C:38](=[O:48])[N:39]([CH:40]1[CH2:45][CH2:44][C:43](=[CH:2][O:3][CH3:4])[CH2:42][CH2:41]1)[CH3:47])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 58562802Benzyl methyl4-oxocyclohexylcarbamate

生成物 1

HCID 69194804(4-Methoxymethylene-cyclohexyl)-methyl-carbamic acid benzyl ester収率 654.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-10 °C

実験手順

A suspension of 749.88 g (2187.5 mmol) (methoxymethyl)triphenylphosphonium chloride in 2.5 l THF was cooled to −10° C. and deprotonated with 245.5 g (2187.5 mmol) potassium t-butoxide. The dark red solution was stirred at 0-5° C. for 0.5 h, cooled to −20° C. and 457.32 g (261.33 mmol) of Methyl-(4-oxo-cyclohexyl)-carbamic acid benzyl ester in 1.251 THF were added over a period of 1.25 h. After 1.3 h at RT, the reaction was treated with 1.75 l aqueous 1M NaHCO3 and stirred for 45 min. The phases were separated, the aqueous phase was extracted with TBME (700 ml), the organic phase was dried (Na2SO4), filtered and evaporated. The residue was suspended in hexane (5 l), cooled (0° C.), filtered and evaporated to give 495.2 g (98%) of (4-Methoxymethylene-cyclohexyl)-methyl-carbamic acid benzyl ester, MS: 289 (M).

後処理

  1. temperaturecooled to −20° C.
  2. waitAfter 1.3 h at RT
  3. stirringstirred for 45 min
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with TBME (700 ml)
  6. dry with materialthe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. temperaturecooled (0° C.)
  10. filtrationfiltered
  11. customevaporated

出典と根拠

ORDレコード
ord-27e1c99bce584b5c894d00f0777aac53
出典データセット
uspto-grants-2005_02
特許番号
US06858651B2

反応ノート

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