tert-Butyl methyl ether → 3,3-Difluoro-3,4-dihydro-2h-thieno[3,4-b][1,4]-dioxepine

HRID 1794558노트

반응식

HRID 1794558 반응식
[F:1][C:2]1([F:18])[CH2:8][O:7][C:6]2=[C:9](C(O)=O)[S:10][C:11](C(O)=O)=[C:5]2[O:4][CH2:3]1.COC(C)(C)C>N1C2C(=CC=CC=2)C=CC=1.[Cr]([O-])([O-])=O.[Cu+2]>[F:18][C:2]1([F:1])[CH2:8][O:7][C:6]2=[CH:9][S:10][CH:11]=[C:5]2[O:4][CH2:3]1

참가 물질

5

반응물 2

HCID 15413tert-Butyl methyl etherHCID 222221443,3-difluoro-3,4-dihydro-2H-thieno[3,4-b][1,4]-dioxepine-6,8-dicarboxylic acid

생성물 1

HCID 222221473,3-Difluoro-3,4-dihydro-2h-thieno[3,4-b][1,4]-dioxepine수율 40%

시약·촉매·용매 2

HCID 178505374HCID 178505374, 화합물촉매HCID 7047Quinoline용매

실험 절차

300 mg (1.07 mmol) of 3,3-difluoro-3,4-dihydro-2H-thieno[3,4-b][1,4]-dioxepine-6,8-dicarboxylic acid was heated at 175° C. with 77 mg of copper chromite in 3.0 mL of quinoline for 1.5 hours. After cooling and mixing with 35 mL of tert-butyl methyl ether, the resulting mixture was washed three times with 2N hydrochloric acid, then three times with deionized water, dried with anhydrous magnesium sulphate and finally evaporated to dryness yielding 138 mg of raw product. The raw product was purified by column chromatography using Kieselgel 60 and cyclohexane as eluant. 82 mg of 3,3-difluoro-3,4-dihydro-2H-thieno[3,4-b][1,4]-dioxepine (M3) was obtained corresponding to a yield of 40% with a melting point of 66–67° C., as characterized by:

후처리

  1. temperatureAfter cooling
  2. washthe resulting mixture was washed three times with 2N hydrochloric acid
  3. dry with materialthree times with deionized water, dried with anhydrous magnesium sulphate
  4. customfinally evaporated to dryness
  5. customyielding 138 mg of raw product
  6. customThe raw product was purified by column chromatography

출처 및 근거

ORD 기록
ord-4273ca3bb90e4b318f48b7e935190d9f
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022811B2

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