Water → 3,3'-(2-Phenylethene-1,1-diyl)bis((trifluoromethoxy)benzene)

HRID 238821

반응식

HRID 238821 반응식
[H-].[Na+].[F:3][C:4]([F:26])([F:25])[O:5][C:6]1[CH:7]=[C:8]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=2)=O)[CH:9]=[CH:10][CH:11]=1.[CH2:27](P(=O)(OCC)OCC)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>C1COCC1.C1OCCOCCOCCOCCOC1>[C:28]1([CH:27]=[C:12]([C:14]2[CH:15]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:7]=[C:6]([O:5][C:4]([F:26])([F:25])[F:3])[CH:11]=[CH:10][CH:9]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 14122Diethyl benzylphosphonateHCID 24758Sodium hydrideHCID 59458637Bis(3-(trifluoromethoxy)phenyl)methanone

생성물 1

HCID 594586043,3'-(2-Phenylethene-1,1-diyl)bis((trifluoromethoxy)benzene)수율 53%

시약·촉매·용매 2

HCID 3633615-Crown-5촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of NaH (60% in oil, 0.24 g, 6 mmol) in dry THF (25 mL) under nitrogen was added 15-crown-5 (0.06 g). The suspension was cooled in an ice bath. Bis(3-(trifluoromethoxy)phenyl)methanone (2.10 g, 6 mmol) and diethyl benzylphosphonate (1.37 g, 6 mmol) were dissolved in THF (12 mL) and added to the suspension. The reaction mixture was stirred at ice bath temperature for 15 min, allowed to warm to rt and stirred overnight. The reaction mixture was poured into water and extracted with ether (2×). The combined ether layers were washed with 10% NaHSO3, sat. NaCl, dried over K2CO3, filtered and purified by ISCO using a gradient of 0-4% EtOAc/hexanes as eluent to give 3,3′-(2-phenylethene-1,1-diyl)bis((trifluoromethoxy)benzene) as a colorless oil (1.34 g, 53% yield). 1H NMR (400 MHz, CDC3) δ ppm 7.33 (m, 2H), 7.2-7.1 (m, 8H), 7.04 (s, 1H), 7.0-6.97 (m, 3H).

후처리

  1. temperatureThe suspension was cooled in an ice bath
  2. additionadded to the suspension
  3. stirringstirred overnight
  4. extractionextracted with ether (2×)
  5. washThe combined ether layers were washed with 10% NaHSO3, sat. NaCl
  6. dry with materialdried over K2CO3
  7. filtrationfiltered
  8. custompurified by ISCO

출처 및 근거

ORD 기록
ord-b1e8745ba23c4c0b9ca311b14b92b4a2
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642576B2

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