Ammonium fluoride → Ethyl 8-allyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylate

HRID 854918노트

반응식

HRID 854918 반응식
I[C:2]1[CH:3]=[C:4]([O:21][C:22]([F:25])([F:24])[F:23])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])F)[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7]2.[CH2:26]([CH:30]([Sn])C=C(CCCC)CCCC)[CH2:27]CC.[NH4+].[F-:43]>C1(C)C=CC=CC=1.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>[CH2:30]([C:2]1[CH:3]=[C:4]([O:21][C:22]([F:25])([F:24])[F:23])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:14])([F:15])[F:43])[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7]2)[CH:26]=[CH2:27]

참가 물질

6

반응물 3

HCID 25516Ammonium fluorideHCID 86589045TributylallyltinHCID 86599457ethyl 8-iodo-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

생성물 1

HCID 87870734Ethyl 8-allyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylate수율 94%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

To a mixture of ethyl 8-iodo-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 21a, Step 2 (1.00 g, 2.07 mmole) and Pd(PPh3)4 (0.239 g, 0.207 mmole) in anhydrous toluene (50 mL) under a dry N2 atmosphere was added tributylallyltin (0.707 mL, 2.28 mmole). The mixture was refluxed for 16 h and 20% NH4F solution (50 mL) was added. The mixture was stirred for 1 h and extracted with EtOAc (200 mL). The extract was washed with brine (100 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica chromatography (9:1 hexanes:EtOAc) gave 0.770 g (94% yield) of the product as a yellow oil: EIHRMS m/z 396.0769 (M+, C17H14F6O4, Calc'd 396.0796).

후처리

  1. temperatureThe mixture was refluxed for 16 h
  2. extractionextracted with EtOAc (200 mL)
  3. washThe extract was washed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica chromatography (9:1 hexanes:EtOAc)

출처 및 근거

ORD 기록
ord-c7396466f8424b1b8561efa7db04ad2e
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259266B2

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