Sulfuric Acid → HCID 54720230、化合物

HRID 985429ノート

反応式

HRID 985429 の反応式
[OH:1][C:2]1[CH:6]([CH3:7])[O:5][C:4](=[O:8])[CH:3]=1.[C:9](O)([CH3:12])([CH3:11])[CH3:10].S(=O)(=O)(O)O>>[C:9]([C:3]1[C:4](=[O:8])[O:5][CH:6]([CH3:7])[C:2]=1[OH:1])([CH3:12])([CH3:11])[CH3:10]

参加物

4

反応物 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 546921524-Hydroxy-5-methyl-5H-furan-2-one

生成物 1

HCID 54720230HCID 54720230、化合物収率 13%

反応条件

温度
40 °C

実験手順

4-Hydroxy-5-methyl-5H-furan-2-one (15.9 g, 0.14 mol) was dissolved in tert-butanol (13.9 ml, 0.147 mol) with concentrated sulfuric acid (7.8 ml, 0.147 mol) and heated at 40° C. for 4 days. The reaction mixture was allowed to cool and was partitioned between water (75 ml) and diethyl ether (75 ml). The organic layer was separated and dried (Na2SO4), filtered and concentrated under vacuum. Chromatography on silica gel with diethyl ether as eluent gave a crude product which was further purified by chromatography on silica gel with dichloromethane as eluent then triturated with diethyl ether to give 3-tert-butyl-4-hydroxy-5-methyl-5H-furan-2-one (3.1 g) as a white solid. 1H NMR (360 MHz, CDCl3) δ 1.34 (9H, s), 1.46 (3H, d, J=6.7 Hz), 4.69 (1H, q, J=6.7 Hz).

後処理

  1. temperatureto cool
  2. customwas partitioned between water (75 ml) and diethyl ether (75 ml)
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customChromatography on silica gel with diethyl ether as eluent gave a crude product which
  8. customwas further purified by chromatography on silica gel with dichloromethane as eluent
  9. customthen triturated with diethyl ether

出典と根拠

ORDレコード
ord-f9f54c0bd3e94126a169a4d41cb4db97
出典データセット
uspto-grants-2005_03
特許番号
US06872720B2

反応ノート

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