Methyl iodide → 4-(1,1-Dimethyl-2-butynyl)anisole

HRID 481524

반응식

HRID 481524 반응식
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)([CH3:7])[CH:3]=[C:4](Br)Br.[Li][CH2:17]CCC.CI>C1COCC1>[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)([CH3:7])[C:3]#[C:4][CH3:17]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 190664224-(1,1-Dimethyl-3,3-dibromo-2-propenyl)anisoleHCID 178418339Butyllithium

생성물 1

HCID 190665084-(1,1-Dimethyl-2-butynyl)anisole수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of Compound 53 (335 mg, 1.00 mmol) in THF (10 ml) was added n-BuLi (1.69M in hexane, 1.19 ml, 2.01 mmol) at -78° C. under N2, then warmed up to 0° C., and stirred for 1.5 h. MeI (213 mg, 1.50 mmol) was added, and stirred for 1.5 h at 0° C. The mixture was quenched by the addition of NH4Cl aq., and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated. This was purified by SiO2 chromatography to give Compound 54 (162 mg, 86%) as a colorless oil.

후처리

  1. stirringstirred for 1.5 h at 0° C
  2. customThe mixture was quenched by the addition of NH4Cl aq.
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThis was purified by SiO2 chromatography

출처 및 근거

ORD 기록
ord-2ea3746090b5481bb563e3337c69d2d3
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789423

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