Boron trifluoride → 3-Carboethoxy-1,8,8-trimethylbicyclo[3,2,1]octane-2,4-dione

HRID 1940476노트

반응식

HRID 1940476 반응식
[C:1]12([CH3:12])[C:9]([CH3:11])([CH3:10])[CH:6]([CH2:7][CH2:8]1)[C:4](=[O:5])[C:2]2=[O:3].[N+](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N-].B(F)(F)F>CCOCC>[C:16]([CH:15]1[C:4](=[O:5])[CH:6]2[C:9]([CH3:10])([CH3:11])[C:1]([CH3:12])([CH2:8][CH2:7]2)[C:2]1=[O:3])([O:18][CH2:19][CH3:20])=[O:17]

참가 물질

5

반응물 3

HCID 6356Boron trifluorideHCID 12192Ethyl diazoacetateHCID 25208Bornane-2,3-dione

생성물 1

HCID 189798163-Carboethoxy-1,8,8-trimethylbicyclo[3,2,1]octane-2,4-dione

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of (±) camphorquinone [(1,7,7) -trimethylbicyclo[3,2,1]-heptane-2,3-dione] (15.0 g, 90.24 mmol) and ethyl diazoacetate (11.8 g, 103.7 mmol) in 120 ml of ether is added, at 0°, BF3.ether (4 ml). The mixture is stirred at RT for 24 hr. The reaction mixture is extracted with 5% K2CO3 /H2O until no polar ethyl carboxyl dione remains. The combined aqueous extracts are acidified with conc. HCl and extracted with ether. The combined organic extracts are dried and evaporated to dryness to give crystalline 3-carboethoxy-1,8,8-trimethylbicyclo[3,2,1 ]octane-2,4-dione.

후처리

  1. extractionThe reaction mixture is extracted with 5% K2CO3 /H2O until no polar ethyl carboxyl dione
  2. extractionextracted with ether
  3. customThe combined organic extracts are dried
  4. customevaporated to dryness

출처 및 근거

ORD 기록
ord-2cdd18bf0c834098959cbbfe3fff974c
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05700762

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