Diethyl Ether → 2-(1-benzyl-2-hydroxymethyl-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol

HRID 1724028ノート

反応式

HRID 1724028 の反応式
C(N1C2C(=CC=CC=2)C([C:17]([OH:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=C1CO[Si](C(C)C)(C(C)C)C(C)C)C1C=CC=CC=1.[F-].C([N+:44]([CH2:53][CH2:54][CH2:55][CH3:56])([CH2:49][CH2:50][CH2:51][CH3:52])[CH2:45][CH2:46][CH2:47][CH3:48])CCC.[NH4+].[Cl-].C[CH2:60][O:61]CC.[CH2:64]1[CH2:68]OC[CH2:65]1>>[CH2:53]([N:44]1[C:45]2[C:51](=[CH:52][C:48]([C:17]([OH:26])([C:22]([F:23])([F:24])[F:25])[C:18]([F:20])([F:19])[F:21])=[CH:47][CH:46]=2)[CH:50]=[C:49]1[CH2:60][OH:61])[C:54]1[CH:55]=[CH:56][CH:68]=[CH:64][CH:65]=1

参加物

6

反応物 5

HCID 3283Diethyl EtherHCID 8028Tetrahydrofuran2 回HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 867608102-(1-benzyl-2-triisopropylsilanyloxymethyl-1H-indol--yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol

生成物 1

HCID 115604542-(1-benzyl-2-hydroxymethyl-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol

実験手順

To a solution of 0.93 g (1.66 mmol) of 2-(1-benzyl-2-triisopropylsilanyloxymethyl-1H-indol--yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol in 10 mL of THF were added 1.66 mL (1.66 mmol) of a 1 M solution of tetrabutyl ammonium fluoride in THF. The mixture was stirred at RT for 1 h and poured into a mixture of a saturated aqueous solution of NH4Cl and Et2O. The phases were separated and the aqueous one was extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 1.0 g (quantitative) of 2-(1-benzyl-2-hydroxymethyl-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol, light yellow semisolid, MS: 402 (M−H)−.

後処理

  1. customThe phases were separated
  2. extractionthe aqueous one was extracted with Et2O
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. customevaporated

出典と根拠

ORDレコード
ord-5981af55b50b4093886a2e71a3d70f1a
出典データセット
uspto-grants-2009_02
特許番号
US07485652B2

反応ノート

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