Methyl iodide → Methyl 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzoate

HRID 1443419ノート

反応式

HRID 1443419 の反応式
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.IC.[C:22](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:22])=[O:16])=[CH:18][CH:19]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 595560954-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)benzoic acid

生成物 1

HCID 22730331Methyl 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzoate収率 72%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzoic acid (572 mg, 2.20 mmol), iodomethane (140 μL, 2.24 mmol), and cesium carbonate (710 mg, 2.17 mmol) in 6 mL of DMF was stirred at rt for 16 h. The mixture was diluted with H2O (10 mL) and extracted with Et2O (100 mL). The organic layer was separated, dried over MgSO4, and concentrated. Chromatography on a Biotage 40S cartridge using 3:17 v/v EtOAc/hexanes as the eluant afforded 399 mg (72%) of the title compound.

後処理

  1. extractionextracted with Et2O (100 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-dbc79623aa6c48939795b3758fb1fa55
出典データセット
uspto-grants-2010_02
特許番号
US07659294B2

反応ノート

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