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Sodium Carbonate → tert-butyl (E)-4-[3-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)allyl]piperidine-1-carboxylate

HRID 1750002
ノート
印刷プレビュー

反応式

HRID 1750002 の反応式
CC1(C)C(C)(C)OB(/[CH:9]=[CH:10]/[CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)O1.I[C:27]1[C:35]2[O:34][CH2:33][C:32](=[O:36])[C:31]=2[CH:30]=[CH:29][C:28]=1[O:37][CH3:38].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:38][O:37][C:28]1[CH:29]=[CH:30][C:31]2[C:32](=[O:36])[CH2:33][O:34][C:35]=2[C:27]=1/[CH:9]=[CH:10]/[CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:16][CH2:17]1
参加物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 10340Sodium CarbonateHCID 712788737-iodo-6-methoxybenzofuran-3(2H)-oneHCID 86682085tert-Butyl (E)-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)piperidine-1-carboxylate

生成物 1

HCID 86682086tert-butyl (E)-4-[3-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)allyl]piperidine-1-carboxylate収率 16.1%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 312751,4-Dioxane溶媒

実験手順

A solution of tert-butyl (E)-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]piperidine-1-carboxylate (0.176 g, 0.501 mmol) in 1,4-dioxane (5 mL) was added with 7-iodo-6-methoxybenzofuran-3(2H)-one (0.145 g, 0.501 mmol) synthesized in Example B46, Step 2, 2 M aqueous sodium carbonate (0.750 mL, 1.50 mmol) and tetrakis(triphenylphosphine)palladium (0.0579 g, 0.0501 mmol), and the mixture was refluxed for 12 hours by heating. The reaction mixture was cooled to room temperature, concentrated, and added with water, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl (E)-4-[3-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)allyl]piperidine-1-carboxylate (0.0313 g, 16%).

後処理

  1. temperaturethe mixture was refluxed for 12 hours
  2. temperatureby heating
  3. concentrationconcentrated
  4. additionadded with water
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-ddc1156d22d143a0a04cd0b9dda7b75d
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09156827B2

反応ノート

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