Imidazole → HCID 57912293、化合物

HRID 389012ノート

反応式

HRID 389012 の反応式
[N+:1]([C:4]1[C:9]([CH2:10][OH:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:12][OH:13])([O-:3])=[O:2].CN(C=O)C.N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C(OCC)(=O)C>[Si:24]([O:13][CH2:12][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[C:9]([CH2:10][OH:11])[CH:8]=[CH:7][CH:6]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

参加物

6

反応物 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 13519807[3-(hydroxymethyl)-2-nitrophenyl]methanol

生成物 1

HCID 57912293HCID 57912293、化合物収率 80%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a clean, dry round-bottom flask was added 2-nitro-1,3-benzenedimethanol (818 mg, 4.47 mmol), anhydrous DMF (40 mL), and imidazole (304.2 mg, 4.47 mmol). The solution was maintained at 0° C. while tert-butyldimethylsilylchloride (337 mg, 2.24 mmol) was slowly added. The resulting pale yellow solution was allowed to warm to room temperature and stirred overnight under argon before being diluted with ethyl acetate (100 mL), washed with water (5×50 mL), dried over MgSO4, filtered, concentrated on a rotary evaporator, and purified by silica gel chromatography (30% EtOAc:hexanes) to yield 3-(tert-butyldimethylsilyloxymethyl)-2-nitro-hydroxymethylbenzene as a yellow oil which crystallized upon further solvent removal in vacuo. The excess 2-nitro-1,3-benzenedimethanol was recovered and re-subjected to the reaction conditions to yield Compound 9 in 80% yield after three iterations.

後処理

  1. additionwas slowly added
  2. washwashed with water (5×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator
  6. custompurified by silica gel chromatography (30% EtOAc:hexanes)

出典と根拠

ORDレコード
ord-db8d3721ddc345a59aedcccf81f2c709
出典データセット
uspto-grants-2013_02
特許番号
US08378041B2

反応ノート

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