Trimethylsilyl triflate → 2-[3-Bromo-4-(cyclopropylmethoxy)phenyl]-2-methyl-1,3-dioxolane

HRID 2208137

반응식

HRID 2208137 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:13](=[O:15])[CH3:14])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C[Si](C)(C)[O:30][CH2:31][CH2:32]O[Si](C)(C)C>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:13]2([CH3:14])[O:30][CH2:31][CH2:32][O:15]2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1

참가 물질

5

반응물 3

HCID 65367Trimethylsilyl triflateHCID 818582,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctaneHCID 629080041-[3-Bromo-4-(cyclopropylmethoxy)phenyl]ethanone

생성물 1

HCID 670330682-[3-Bromo-4-(cyclopropylmethoxy)phenyl]-2-methyl-1,3-dioxolane

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 1-(3-bromo-4-cyclopropylmethoxy-phenyl)-ethanone from example B.b13 (14.0 g; 52.0 mmol) in dry dichloromethane (250 mL) was cooled in an ice-bath before addition of trimethylsilyl trifluoro-methane sulfonate (0.23 g; 1.04 mmol) and dropwise addition of 1,2-bis(trimethylsilyloxy)-ethane (13.15 g; 62.4 mmol). The reaction mixture was stirred for two hours, extracted with 1M aqueous NaHCO3 (100 mL) and dried over MgSO4. The crude is purified by column chromatography on silica gel (ethyl acetate/cyclohexane-9:1) to yield the title compound as pale yellow oil.

후처리

  1. extractionextracted with 1M aqueous NaHCO3 (100 mL)
  2. dry with materialdried over MgSO4
  3. customThe crude is purified by column chromatography on silica gel (ethyl acetate/cyclohexane-9:1)

출처 및 근거

ORD 기록
ord-cce35a5fc1f14c97afa03aa8fb964833
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376442B2

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