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

HRID 1443419노트

반응식

HRID 1443419 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-dbc79623aa6c48939795b3758fb1fa55
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659294B2

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