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

HRID 865516

반응식

HRID 865516 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 3283Diethyl Ether용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-66029934cfb6421fb7c42f00022d6593
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05565485

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