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Triethylamine → 1-[2,4-Bis(trifluoromethyl)benzyl]pyrrolidine-3-carbaldehyde

HRID 1620572
ノート
印刷プレビュー

反応式

HRID 1620572 の反応式
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:4]=1[CH2:5][N:6]1[CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7]1.C(N(CC)CC)C.O.C(OCC)(=O)C>CS(C)=O>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:4]=1[CH2:5][N:6]1[CH2:10][CH2:9][CH:8]([CH:11]=[O:12])[CH2:7]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 22728543Water ethylacetateHCID 86678748{1-[2,4-Bis(trifluoromethyl)benzyl]pyrrolidin-3-yl}methanol

生成物 1

HCID 866787491-[2,4-Bis(trifluoromethyl)benzyl]pyrrolidine-3-carbaldehyde収率 75.1%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of {1-[2,4-bis(trifluoromethyl)benzyl]pyrrolidin-3-yl}methanol (4.69 g) and triethylamine (5.99 mL) in dimethyl sulfoxide (50 mL) was added sulfur trioxide pyridine complex (6.84 g), and the mixture was stirred at room temperature for 4 hr. Water/ethyl acetate were added to the reaction mixture, and the organic layer was separated, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.50 g).

後処理

  1. customthe organic layer was separated
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-aa9e3cb6e2f44551b29688e50a07caaa
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08772277B2

反応ノート

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