Edetate Trisodium → Racemic ethyl cis-3-acetoxymethyl-2,2-dimethylcyclopropanecarboxylate

HRID 2078487

반응식

HRID 2078487 반응식
[C:1]([O:4][CH2:5][CH:6]=[C:7]([CH3:9])[CH3:8])(=[O:3])[CH3:2].[N+](=C[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N-].[CH2:18](N(CC([O-])=O)CC(O)=O)CN(CC([O-])=O)CC([O-])=O.[Na+].[Na+].[Na+].CC[C@@H]1N2C(N(C3C=CC(F)=CC=3)C(=O)[C@H]2CC2C3C(NC1=2)=CC=CC=3)=O>C(OCC)(=O)C.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)C([O-])=O)C=CC=CC=1.[Rh+3].C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)C([O-])=O)C=CC=CC=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)C([O-])=O)C=CC=CC=1>[C:1]([O:4][CH2:5][C@@H:6]1[C@H:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]1([CH3:18])[CH3:9])(=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 9008Edetate TrisodiumHCID 12192Ethyl diazoacetateHCID 14489Prenyl acetateHCID 24978618trans-Body

생성물 1

HCID 67120924Racemic ethyl cis-3-acetoxymethyl-2,2-dimethylcyclopropanecarboxylate

시약·촉매·용매 2

HCID 71464060Rhodium triphenyl acetate촉매HCID 8857Ethyl Acetate용매2회

반응 조건

온도
50 °C

실험 절차

Rhodium triphenylacetate, 6.78 mg (0.01 mmol), was dissolved in 9.0 g of ethyl acetate, and 2.56 g (20.0 mmol) of 1-acetoxy-3-methyl-2-butene was added, then, the temperature thereof was raised to 50° C. Into this solution, a solution composed of 1.14 g (10.0 mmol) of ethyl diazoacetate and 3.6 g of ethyl acetate was dropped over a period of 2 hours, and the mixture was, thermally kept at the same temperature for 0.5 hours. To this solution was added an aqueous solution containing 0.5 mol of trisodium ethylenediaminetetraacetate per liter and the solution was mixed and separated, and a solution containing 1.82 g of ethyl 3-acetoxymethyl-2,2-dimethylcyclopropanecarboxylate was obtained (yield based on ethyl diazoacetate: 84.8%). The cis body/trans body ratio was 72/28.

후처리

  1. additionwas dropped over a period of 2 hours
  2. additionTo this solution was added an aqueous solution
  3. additionthe solution was mixed
  4. customseparated
  5. additiona solution containing 1.82 g of ethyl 3-acetoxymethyl-2,2-dimethylcyclopropanecarboxylate
  6. customwas obtained
  7. custom(yield based on ethyl diazoacetate: 84.8%)

출처 및 근거

ORD 기록
ord-d0790c9840c94fa5bdb44412e7d5bb07
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928253B2

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