Sulfuric Acid → 7-(4-Hydroxycyclopent-2-en-1-on-2-yl)-5-heptynoic acid

HRID 1032505ノート

反応式

HRID 1032505 の反応式
CO[C:3]1([CH2:10][CH2:11][C:12]#[C:13][CH2:14][CH2:15][CH2:16][C:17]([O:22]C)([O:20]C)OC)[CH:7]=[CH:6][CH:5]([O:8]C)O1.O.P([O-])(O)(O)=[O:26].[Na+].O1CCOCC1.S(=O)(=O)(O)O>P([O-])([O-])(O)=O.[Na+].[Na+].O>[OH:26][CH:7]1[CH2:6][C:5](=[O:8])[C:10]([CH2:11][C:12]#[C:13][CH2:14][CH2:15][CH2:16][C:17]([OH:20])=[O:22])=[CH:3]1

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 221661452,5-Dihydro-2,5-dimethoxy-2-(8,8,8-trimethoxy-3-octynyl)furan

生成物 1

HCID 147744257-(4-Hydroxycyclopent-2-en-1-on-2-yl)-5-heptynoic acid収率 112.5%

試薬・触媒・溶媒 2

HCID 24203Sodium Phosphate, Dibasic触媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

A stirred mixture of 7.1 g of 2,5-dihydro-2,5-di- methoxy-2-(8,8,8-trimethoxy-3-octynyl)furan, 2.76 g of sodium dihydrogen phosphate monohydrate, 140 mg of disodium hydrogen phosphate, 60 ml of dioxane and 40 ml of water was boiled under reflux for 19 hours, then cooled to 50° C. and treated dropwise with 4.1 ml of concentrated sulfuric acid. The resulting solution was boiled under reflux for 12 hours, cooled and partitioned with ether and brine. The ether layer was separated, washed with brine, dried and concentrated, giving 5.0 g of crude 7-(4-hydroxycyclopent-2-en-1-on-2-yl)-5-heptynoic acid. This crude product was dissolved in 40 ml of pyridine and the stirred solution treated at 0° to 10° C. with 10.5 ml of hexamethyldisilizane followed by 6.3 ml of chlorotrimethylsilane. The resulting mixture was stirred at 25° C. for 3 hours and then concentrated to dryness at 30° C. The residue was extracted with hexane, the extract filtered through diatomaceous earth and concentrated. The residue was distilled at 0.11 mm on a Kugelrohr at 155°-170° C., giving 1.66 g of the desired compound as an oil.

後処理

  1. temperatureunder reflux for 19 hours
  2. temperatureunder reflux for 12 hours
  3. temperaturecooled
  4. custompartitioned with ether and brine
  5. customThe ether layer was separated
  6. washwashed with brine
  7. customdried
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-ae5f0a12fbc64408afa0a03046e1bba2
出典データセット
uspto-grants-1990_09
特許番号
US04958037

反応ノート

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