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

HRID 481524

反応式

HRID 481524 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2ea3746090b5481bb563e3337c69d2d3
出典データセット
uspto-grants-1998_08
特許番号
US05789423

関連ノート

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