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

HRID 1270428ノート

反応式

HRID 1270428 の反応式
[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

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 74341221-(Benzhydryloxy)-2-nitrobenzeneHCID 178418507HCID 178418507、化合物

生成物 1

HCID 150540087-(Diphenylmethoxy)-1H-indole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ec4cca4f16c2406583ef840a41861f94
出典データセット
uspto-grants-2007_04
特許番号
US07202255B2

反応ノート

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