Hydrochloric Acid → 1,2,3,5,6,7-Hexahydro-s-indacene

HRID 1276539ノート

反応式

HRID 1276539 の反応式
[C:1]1(=O)[C:12]2[C:4](=[CH:5][C:6]3[CH2:7][CH2:8][CH2:9][C:10]=3[CH:11]=2)[CH2:3][CH2:2]1.Cl.[H][H]>[Pd].C(O)C>[CH2:3]1[C:4]2[C:12](=[CH:11][C:10]3[CH2:9][CH2:8][CH2:7][C:6]=3[CH:5]=2)[CH2:1][CH2:2]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 109318913,5,6,7-tetrahydro-s-indacen-1(2H)-oneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 1363211,2,3,5,6,7-Hexahydro-s-indacene収率 73.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A mixture of 3,5,6,7-tetrahydro-2H-s-indacen-1-one (90 grams), ethanol (1 L), 10% palladium on carbon (1-2 grams) and concentrated hydrochloric acid (50 mL) was hydrogenated on a Parr shaker at room temperature until hydrogen uptake ceased. The mixture was filtered through a Celite pad. The pad was washed with 1 L diethyl ether. The filtrate was diluted with water and the organic phase was separated. The aqueous phase was extracted with 1 L of ether, and the combined ether extracts were washed with water, saturated sodium bicarbonate solution and brine. The ether extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting pale yellow solid was recrystallized from methanol to afford 61 grams of the title compound as colorless crystals, m.p. 56.6-58.5° C.

後処理

  1. filtrationThe mixture was filtered through a Celite pad
  2. washThe pad was washed with 1 L diethyl ether
  3. additionThe filtrate was diluted with water
  4. customthe organic phase was separated
  5. extractionThe aqueous phase was extracted with 1 L of ether
  6. washthe combined ether extracts were washed with water, saturated sodium bicarbonate solution and brine
  7. dry with materialThe ether extracts were dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe resulting pale yellow solid was recrystallized from methanol

出典と根拠

ORDレコード
ord-1af03601112f412593fed240a51ee982
出典データセット
uspto-grants-2000_12
特許番号
US06166064

反応ノート

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