Acetone → 4-Ethoxycarbonyl-1,2-cyclopentanediol

HRID 1165077ノート

反応式

HRID 1165077 の反応式
C[N+]1([O-])CC[O:5]CC1.O.[CH:10]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])CC=C[CH2:11]1.S(=O)(O)[O-].[Na+].[CH3:25][C:26]([CH3:28])=[O:27]>[Os](=O)(=O)(=O)=O.C(OCC)(=O)C.CCCCCC>[CH2:18]([O:17][C:15]([CH:10]1[CH2:28][CH:26]([OH:27])[CH:25]([OH:5])[CH2:11]1)=[O:16])[CH3:19]

参加物

8

反応物 5

HCID 180Acetone2 回HCID 962WaterHCID 82029Methyl morpholine oxideHCID 5314991Ethyl 3-Cyclopentene-1-carboxylateHCID 23665763Sodium Bisulfite

生成物 1

HCID 144761474-Ethoxycarbonyl-1,2-cyclopentanediol

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

A solution containing 84.6 g of N-methylmorpholine N-oxide, 1 g of osmium tetroxide, 230 ml of water and 115 ml of acetone was allowed to stir for 30 minutes at room temperature. To this stirred mixture was added, very slowly over at least 8 hours, a solution of 80 g of ethyl 3-cyclopentene-1-carboxylate in 115 ml of acetone. The stirred mixture was heated at 50° C. for 2 hours to complete the reaction (verified by TLC examination using ethyl acetate/hexane 70/30). Sodium bisulfite (~10 g) was added, the stirring continued for a further 15 minutes, and the mixture filtered through Celite. The pH of the filtrate was adjusted to 7 by the addition of 12 N sulfuric acid (37 ml), the acetone evaporated, the pH of the residual solution adjusted to 2 with 12 N sulfuric acid (13 ml) and the solution extracted with ethyl acetate (4×250 ml). Evaporation of the dried ethyl acetate solution gave 4-ethoxycarbonyl-1,2-cyclopentanediol.

後処理

  1. additionTo this stirred mixture was added, very slowly over at least 8 hours
  2. temperatureThe stirred mixture was heated at 50° C. for 2 hours
  3. waitthe stirring continued for a further 15 minutes
  4. filtrationthe mixture filtered through Celite
  5. additionThe pH of the filtrate was adjusted to 7 by the addition of 12 N sulfuric acid (37 ml)
  6. customthe acetone evaporated
  7. extractionthe solution extracted with ethyl acetate (4×250 ml)
  8. customEvaporation of the dried ethyl acetate solution

出典と根拠

ORDレコード
ord-684e9ce17e94439d971a4498b89c7da3
出典データセット
uspto-grants-1990_03
特許番号
US04906755

反応ノート

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