Imidazole → 9-Methoxymethyl-9-[(tert-butyldimethylsilyl)oxymethyl]-fluorene

HRID 2252527ノート

反応式

HRID 2252527 の反応式
[CH3:1][O:2][CH2:3][C:4]1([CH2:17][OH:18])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.N1C=CN=C1.C(N(CC)CC)C.[Si:31](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>CN(C)C=O.O>[CH3:1][O:2][CH2:3][C:4]1([CH2:17][O:18][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2

参加物

7

反応物 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 226391039-(Methoxymethyl)-9H-fluorene-9-methanol

生成物 1

HCID 226391259-Methoxymethyl-9-[(tert-butyldimethylsilyl)oxymethyl]-fluorene収率 86.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

1 g of 9-methoxymethyl-9-hydroxymethyl-fluorene (4.16 mmol) was dissolved in 10 ml of N,N-dimethyl formamide, and 0.14 g (2.08 mmol) of imidazole was added thereto. The solution was cooled in ice-water bath to below 5° C., and 0.87 ml of triethyl amine (6.24 mmol) was added thereto. After stirring for 5 minutes, 0.88 g of tert-butyldimethylsilyl chloride (5.82 mmol) in 10 ml of N,N-dimethyl formamide was added drop-wise to the reaction mixture, and the mixture was stirred for further 2 hours, followed by stirring at room temperature for 1 hour. The reaction mixture was diluted with 10 ml of water, and extracted using 30 ml of dichloromethane. The organic phase was wished twice with 20 ml of water, dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated to give 1.28 g of 9-methoxymethyl-9-[(tert-butyldimethylsilyl )oxymethyl]-fluorene crude product as pale yellow liquid. The crude product was purified by column chromatography using petroleum ether as eluent, to give colorless pure compound.

後処理

  1. stirringthe mixture was stirred for further 2 hours
  2. stirringby stirring at room temperature for 1 hour
  3. extractionextracted
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe filtrate was evaporated

出典と根拠

ORDレコード
ord-4cf6de34f26b4e2fb12f0a95b9820c90
出典データセット
uspto-grants-2008_01
特許番号
US07323431B2

反応ノート

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