Bromine → Ethyl 2-(5-oxo-1-cyclopentenyl)acetate

HRID 442085ノート

反応式

HRID 442085 の反応式
C([O:4][C:5]1[CH2:9][CH2:8][CH2:7][C:6]=1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(=O)C.BrBr.[Br-].[Li+].C(=O)([O-])[O-].[Li+].[Li+].Cl.NO.C([O-])(=O)C.[Na+]>CN(C)C=O.C(O)C.COCCO.CCCCCCC>[C:11]([CH2:10][C:6]1[C:5](=[O:4])[CH2:9][CH2:8][CH:7]=1)([O:13][CH2:14][CH3:15])=[O:12]

参加物

10

反応物 5

HCID 24408BromineHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 203242041-Acetoxy-2-(carbethoxymethyl)cyclopent-1-eneHCID 86734010Trilithium;bromide;carbonate

生成物 1

HCID 11355698Ethyl 2-(5-oxo-1-cyclopentenyl)acetate

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒HCID 80192-Methoxyethanol溶媒HCID 8900Heptane溶媒

実験手順

In the manner described in Example 28, treatment of 1-acetoxy-2-(carbethoxymethyl)cyclopent-1-ene (Example 21) with bromine and subsequent dehydrobromination with lithium bromide-lithium carbonate in N,N-dimethylformamide gives an amber oil. This material is subjected to chromatography on diatomaceous earth using an n-heptane:methyl cellosolve system. Removal of the solvent from hold back volume 4.5-4.7 gives an oil which is then further treated with hydroxylamine hydrochloride, sodium acetate in ethanol at room temperature for 18 hours to give the desired product; b.p. 71° C. (0.12 mm); λmaxMeOH 222 mμ (10,300); λmax 5.75, 5.85, 6.15, 8.65 μ.

後処理

  1. customgives an amber oil
  2. customRemoval of the solvent from hold back volume 4.5-4.7
  3. customgives an oil which

出典と根拠

ORDレコード
ord-8a1461e271344a838c3083b4217f3626
出典データセット
uspto-grants-1977_08
特許番号
US04044043

反応ノート

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