Trityl chloride → 2-Bromo-1,4-bis(trityloxymethyl)benzene

HRID 499724ノート

反応式

HRID 499724 の反応式
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([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.[Br:21][C:22]1[CH:27]=[C:26]([CH2:28][OH:29])[CH:25]=[CH:24][C:23]=1[CH2:30][OH:31].C(N([CH2:37][CH3:38])CC)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[Br:21][C:22]1[CH:27]=[C:26]([CH2:28][O:29][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:25]=[CH:24][C:23]=1[CH2:30][O:31][C:1]([C:38]1[CH:37]=[CH:19][CH:14]=[CH:15][CH:16]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

6

反応物 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 18676617(2-Bromo-4-hydroxymethylphenyl)methanol

生成物 1

HCID 684580852-Bromo-1,4-bis(trityloxymethyl)benzene収率 18.1%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

Under a nitrogen stream, to a solution of trityl chloride (11.58 g, 41.6 mmol) and (2-bromo-4-hydroxymethylphenyl)methanol (4.1 g, 18.9 mmol) in DMF (12 ml), triethylamine (5.8 ml, 41.6 mmol) and DMAP (369.2 mg, 3.02 mmol) were added and the mixture was stirred for 18 hours at room temperature. The reaction mixture was evaporated under reduced pressure to remove the solvent and then extracted with methylene chloride. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then evaporated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:2)) to give the titled compound (2.4 g, 18%).

後処理

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customto remove the solvent
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:2))

出典と根拠

ORDレコード
ord-8ccba11ff0d24bf381beccbd5c88c6d2
出典データセット
uspto-grants-2010_08
特許番号
US07767651B2

反応ノート

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