Allyl bromide → 2-(2-Allyloxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047661ノート

反応式

HRID 1047661 の反応式
[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[OH:24])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:33][CH:34]=[CH2:35]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[O:24][CH2:35][CH:34]=[CH2:33])[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14]1)=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 593140982-(2-Hydroxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

生成物 1

HCID 593142442-(2-Allyloxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester収率 91%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of 2-(2-hydroxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (3) (300 mg, 0.88 mmol), anhydrous Cs2CO3 (573 mg, 1.76 mmol), and KI (30 mg, 0.18 mmol) in DMF (8 mL) is added 3-bromo-propene (90 μL, 1.06 mmol). The resulting reaction suspension is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (30 mL) and washed with water (1×5 mL) and brine (2×5 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (120 g silica gel, gradient elution: 10-30% EtOAc in heptane) to give a pure product (4) as white solid (303 mg, 91%).

後処理

  1. customThe resulting reaction suspension
  2. customAfter the removal of DMF in vacuo
  3. dissolutionthe residue is dissolved in EtOAc (30 mL)
  4. washwashed with water (1×5 mL) and brine (2×5 mL)
  5. dry with materialThe organic layer is dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash column chromatography (120 g silica gel, gradient elution: 10-30% EtOAc in heptane)

出典と根拠

ORDレコード
ord-61ccb3d5c56d4232893c446e1c4743e5
出典データセット
uspto-grants-2013_10
特許番号
US08569535B2

反応ノート

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