Acetone → 4-Ethoxycarbonyl-1,2-cyclopentanediol

HRID 1165077노트

반응식

HRID 1165077 반응식
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]

참가 물질

8

반응물 5

HCID 180Acetone2회HCID 962WaterHCID 82029Methyl morpholine oxideHCID 5314991Ethyl 3-Cyclopentene-1-carboxylateHCID 23665763Sodium Bisulfite

생성물 1

HCID 144761474-Ethoxycarbonyl-1,2-cyclopentanediol

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 21226206Ethyl acetate hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-684e9ce17e94439d971a4498b89c7da3
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04906755

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