Acetic Acid → HCID 21453522、化合物

HRID 436248ノート

反応式

HRID 436248 の反応式
[CH3:1][C@@:2]12[CH2:11][CH2:10][CH2:9][C@H:8]([CH3:12])[C:7]1=[CH:6][C:5](=[O:13])[CH2:4][CH2:3]2.CC([O-])(C)C.[K+].C(O)(=O)C.C([O-])(O)=O.[Na+]>C(O)(C)(C)C>[CH3:1][C:2]12[CH2:11][CH2:10][CH2:9][C:8]([CH3:12])=[C:7]1[CH2:6][C:5](=[O:13])[CH2:4][CH2:3]2

参加物

6

反応物 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 6428338HCID 6428338、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 21453522HCID 21453522、化合物収率 90%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

A solution of 2.0 g (11.5 mM) of trans-6,10-dimethyl-bicyclo[4.4.0]dec-1-en-3-one and 12.0 g (ca. 110 mM) of potassium ter-butylate in 75 ml of ter-butanol, has been stirred during 2 hr at room temperature under an inert atmosphere of nitrogen. 400 ml of a 10% aqueous solution of acetic acid were then added thereto and the thus obtained mixture rapidly neutralized with a saturated aqueous solution of NaHCO3. By extraction with ether followed by washing, drying, evaporation and purification by column chromatography on silicagel (elution with CH2Cl2), there were obtained 1.80 g (90% yield) of the desired product. IR (neat) : 1710, 1600 cm-1NMR (CCl4) : 1.20 (3H,s); 1.58 (3H, large s); 2.27 (2H,t,J=5 cps); 3.10 (2H,m) δ ppm MS : M+ = 178 (57); m/e = 163 (100), 123 (45), 93 (42).

後処理

  1. extractionBy extraction with ether
  2. washby washing
  3. customdrying
  4. customevaporation and purification by column chromatography
  5. washon silicagel (elution with CH2Cl2)

出典と根拠

ORDレコード
ord-18ac633e53074bfa8269b451aea65918
出典データセット
uspto-grants-1977_02
特許番号
US04008184

反応ノート

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