Imidazole → (S)-4-tert-butyldimethylsilyloxy-3-methyl-2-(2-propynyl)cyclopent-2-ene-1-one

HRID 1078996ノート

反応式

HRID 1078996 の反応式
[OH:1][C@H:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][C:9]#[CH:10])=[C:3]1[CH3:11].N1C=CN=C1.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18].C(O)(=O)C(O)=O>CN(C)C=O>[Si:21]([O:1][C@H:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][C:9]#[CH:10])=[C:3]1[CH3:11])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:24])[CH3:23]

参加物

6

反応物 4

HCID 795ImidazoleHCID 971Oxalic AcidHCID 28928tert-Butyldimethylsilyl chlorideHCID 1569974-Hydroxy-3-methyl-2-(prop-2-yn-1-yl)cyclopent-2-en-1-one

生成物 1

HCID 11043662(S)-4-tert-butyldimethylsilyloxy-3-methyl-2-(2-propynyl)cyclopent-2-ene-1-one収率 86.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

1 (S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one (50.0 g) was dissolved in dry dimethylformamide (600 ml), and imidazole (27.3 g) was added to the dimethylformamide solution. Tert-butyldimethylchlorosilane (55.3 g) was added to the solution under ice-water cooling and the resulting mixture was allowed to react for 2 hours, then for 13 hours at 20° C. The reaction solution was poured into an aqueous oxalic acid solution under ice-water cooling, and extracted three times with diethyl ether (200 ml). The ether layers were combined, and the combined layer was washed with saturated aqueous sodium bicarbonate solution and brine in sequence. After dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The resultant residue was subjected to distillation under reduced pressure to afford (S)-4-tert-butyldimethylsilyloxy-3-methyl-2-(2-propynyl)cyclopent-2-ene-1-one (76.0 g, yield 86.0%) as a pale yellow oil.

後処理

  1. customto react for 2 hours
  2. extractionextracted three times with diethyl ether (200 ml)
  3. washthe combined layer was washed with saturated aqueous sodium bicarbonate solution and brine in sequence
  4. dry with materialAfter dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. distillationThe resultant residue was subjected to distillation under reduced pressure

出典と根拠

ORDレコード
ord-4a4e797b8f314bd1a2c4889ba247d509
出典データセット
uspto-grants-1996_08
特許番号
US05550260

反応ノート

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