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

HRID 2078487

反応式

HRID 2078487 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 71464060Rhodium triphenyl acetate触媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
50 °C

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-d0790c9840c94fa5bdb44412e7d5bb07
出典データセット
uspto-grants-2011_04
特許番号
US07928253B2

関連ノート

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