Ammonium Chloride → 7-(Diphenylmethoxy)-1H-indole

HRID 1270428노트

반응식

HRID 1270428 반응식
[CH:1]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-])=O)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]([Mg]Br)=[CH2:25].[Cl-].[NH4+]>O1CCCC1>[CH:1]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:16]=1[NH:21][CH:25]=[CH:24]2)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 74341221-(Benzhydryloxy)-2-nitrobenzeneHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 150540087-(Diphenylmethoxy)-1H-indole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

11.95 mmol of the compound obtained in Step A above are dissolved, under an inert atmosphere, in 80 ml of anhydrous tetrahydrofuran. The temperature of the reaction mixture is then lowered to −40° C. and then 41.84 mmol of a 1M solution of vinylmagnesium bromide in tetrahydrofuran are added dropwise to the solution, which is then stirred for 2 hours 50 minutes from −40° C. to 0° C. The reaction mixture is then hydrolysed at 0° C. using 100 ml of a saturated aqueous ammonium chloride solution, and the aqueous phase is extracted three times with ethyl acetate. The organic phases are combined, dried over magnesium sulphate, filtered and evaporated. Purification by flash chromatography over silica gel (petroleum ether/ethyl acetate: 9/1) allows the expected product to be isolated.

후처리

  1. customis then lowered to −40° C.
  2. customhydrolysed at 0° C.
  3. extractionthe aqueous phase is extracted three times with ethyl acetate
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash chromatography over silica gel (petroleum ether/ethyl acetate: 9/1)
  8. customto be isolated

출처 및 근거

ORD 기록
ord-ec4cca4f16c2406583ef840a41861f94
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202255B2

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