홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Sodium Carbonate → 2-[3-(3,4-Dihydro-1-naphthyl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole

HRID 1740286
노트
인쇄 미리보기

반응식

HRID 1740286 반응식
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH:8]=1)(=O)=O.[CH3:19][C:20]1([CH3:34])[CH2:24][O:23][C:22]([C:25]2[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=2)=[N:21]1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:7]1([C:27]2[CH:26]=[C:25]([C:22]3[O:23][CH2:24][C:20]([CH3:34])([CH3:19])[N:21]=3)[CH:30]=[CH:29][CH:28]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH:8]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 10967830Methanesulfonic acid, trifluoro-, 3,4-dihydro-1-naphthalenyl esterHCID 218381293-(4,4-Dimethyl-4,5-dihydrooxazol-2-yl)phenyldihydroxyborane

생성물 1

HCID 218381802-[3-(3,4-Dihydro-1-naphthyl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole수율 96.3%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
85 °C

실험 절차

A mixture of 3,4-dihydro-1-(trifluoromethylsulfonyloxy)naphthalene (1.0 g), 3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl-dihydroxyborane (1.1 g), tetrakis(triphenylphosphine)palladium(0) (0.21 g), lithium chloride (0.46 g), 2M sodium carbonate aqueous solution (5.1 ml) in 1,2-dimethoxyethane (12 ml) was heated at 85° C. and stirred vigorously for 3 hours under nitrogen atmosphere. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was partitioned between dichloromethane (35 ml) and 2N sodium carbonate aqueous solution (35 ml) and conc. ammonia solution (2.0 ml). The aqueous layer was extracted again with dichloromethane (35 ml) and the combined organic extracts are dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (30:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give 2-[3-(3,4-dihydro-1-naphthyl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole (1.05 g).

후처리

  1. temperatureAfter being cooled to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between dichloromethane (35 ml) and 2N sodium carbonate aqueous solution (35 ml) and conc. ammonia solution (2.0 ml)
  4. extractionThe aqueous layer was extracted again with dichloromethane (35 ml)
  5. dry with materialthe combined organic extracts are dried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (30:1)
  8. additionThe eluted fractions containing the desired product
  9. customwere collected
  10. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-e79777ee472c43d485b5ae41e270503a
출처 데이터셋
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05968985

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트