Ethyl Acetate → t-Butyldimethylsilyloxy-2,6-dipropyl-4-vinyl benzene

HRID 865516

反応式

HRID 865516 の反応式
[CH2:1]([Li])CCC.[Si:6]([O:13][C:14]1[C:19]([CH2:20][CH2:21][CH3:22])=[CH:18][C:17]([CH:23]=O)=[CH:16][C:15]=1[CH2:25][CH2:26][CH3:27])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].C(OCC)(=O)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[Si:6]([O:13][C:14]1[C:19]([CH2:20][CH2:21][CH3:22])=[CH:18][C:17]([CH:23]=[CH2:1])=[CH:16][C:15]=1[CH2:25][CH2:26][CH3:27])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 19080462t-Butyldimethylsilyloxy-2,6-Dipropyl-4-formylbenzeneHCID 178418339Butyllithium

生成物 1

HCID 19080390t-Butyldimethylsilyloxy-2,6-dipropyl-4-vinyl benzene収率 55.4%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1.0 g (2.80 mmol) of methyl triphenylphosphonium bromide in 5.0 mL of ether at 0° C. was added 1.12 mL (2.5M, 2.80 mmol) of butyllithium. The reaction mixture was stirred for 30 minutes at 0° C. and then 756 mg (2.33 mmol) of the title compound from Example 14 (Step A) was added. After stirring for 1h at room temperature, the reaction mixture was poured into ethyl acetate and washed with water and then saturated aqueous sodium chloride. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. Purification by flash chromotography (silica gel, hexane/ethyl acetate 97:3) gave 411 mg of the title compound.

後処理

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromotography (silica gel, hexane/ethyl acetate 97:3)

出典と根拠

ORDレコード
ord-66029934cfb6421fb7c42f00022d6593
出典データセット
uspto-grants-1996_10
特許番号
US05565485

関連ノート

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