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alpha-Methylene butyrolactone → 3-(Tert-butoxycarbonyl)-2-methyl-6-((2-oxo-2,5-dihydrofuran-3-yl)methyl)benzyl acetate

HRID 132188
ノート
印刷プレビュー

反応式

HRID 132188 の反応式
C(OC(N[C:9]1[C:10]([CH3:21])=[C:11]([C:17](I)=[CH:18][CH:19]=1)[CH2:12][O:13][C:14](=[O:16])[CH3:15])=O)(C)(C)C.[CH2:22]=[C:23]1[CH2:28][CH2:27][O:26][C:24]1=[O:25].[C:29]([O-:32])(=[O:31])C.[K+]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:14]([O:13][CH2:12][C:11]1[C:17]([CH2:22][C:23]2[C:24](=[O:25])[O:26][CH2:27][CH:28]=2)=[CH:18][CH:19]=[C:9]([C:29]([O:32][C:10]([CH3:21])([CH3:11])[CH3:9])=[O:31])[C:10]=1[CH3:21])(=[O:16])[CH3:15]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 68352alpha-Methylene butyrolactoneHCID 517044Potassium AcetateHCID 534147073-(Tert-butoxycarbonylamino)-6-iodo-2-methylbenzyl acetate

生成物 1

HCID 673195833-(Tert-butoxycarbonyl)-2-methyl-6-((2-oxo-2,5-dihydrofuran-3-yl)methyl)benzyl acetate収率 54%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Acetic acid 3-tert-butoxycarbonylamino-6-iodo-2-methyl-benzyl ester (575 mg, 1.4 mmol) was dissolved in N,N-dimethylformamide (2.5 mL). α-Methylene-γ-butyrolactone (190 μL, 2.2 mmol) was added to the mixture followed by potassium acetate (420 mg, 4.3 mmol), and then palladium(II) acetate (16 mg, 0.07 mmol). Reaction mixture was heated at 80° C. for 26 hours. Mixture was cooled to room temperature and partitioned between ethyl acetate and aqueous sodium bicarbonate. Layers were separated. Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Silica gel chromatography afforded the title compound as off-white solid in 54% yield. MS m/e (M−H)−=374.

後処理

  1. customReaction mixture
  2. temperatureMixture was cooled to room temperature
  3. custompartitioned between ethyl acetate and aqueous sodium bicarbonate
  4. customLayers were separated
  5. dry with materialOrganic layer was dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-1afc1224460a4984ab72fe2825ec23a5
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07384930B2

反応ノート

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