Methyl iodide → [4-(Cyclopropylcarbonyl)pheny]methyl-propanedioic acid, dimethyl ester

HRID 1838690

반응식

HRID 1838690 반응식
[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13](OC)=O)=[CH:8][CH:7]=2)=[O:5])[CH2:3][CH2:2]1.CO[C:19](=[O:22])[O:20][CH3:21].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].IC>O1CCCC1.C(OCC)(=O)C.O>[CH:1]1([C:4]([C:6]2[CH:7]=[CH:8][C:9]([CH2:12][CH:13]([C:19]([O:20][CH3:21])=[O:22])[C:19]([O:20][CH3:21])=[O:22])=[CH:10][CH:11]=2)=[O:5])[CH2:2][CH2:3]1

참가 물질

8

반응물 4

HCID 6328Methyl iodideHCID 12021Dimethyl CarbonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 12096482Methyl 2-(4-(cyclopropanecarbonyl)phenyl)acetate

생성물 1

HCID 67524057[4-(Cyclopropylcarbonyl)pheny]methyl-propanedioic acid, dimethyl ester수율 21.1%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

Dissolve 4-(cyclopropylcarbonyl)benzeneacetic acid, methyl ester (1.5 g, 6.0 mmol) and dimethylcarbonate (930 mg, 10.3 mmol) in tetrahydrofuran (10 mL). Add 20 mL (20 mmol) of a 1.0 molar solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran over 0.5 hours. Stir 3 days. Add iodomethane (5.3 g, 35 mmol). Stir 24 hours. Add water and ethyl acetate. Wash organic phase with brine, dry over anhydrous magnesium sulfate and concentrate. Purify by flash chromatography (50 g silica gel, ethyl acetate/heptane as eluent) to give the title compound (315 mg, 16%).

후처리

  1. stirringStir 24 hours
  2. dry with materialWash organic phase with brine, dry over anhydrous magnesium sulfate
  3. concentrationconcentrate
  4. customPurify by flash chromatography (50 g silica gel, ethyl acetate/heptane as eluent)

출처 및 근거

ORD 기록
ord-66d012bc8d1f4719a58a452b1bc7b435
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06673933B2

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