3,4-dihydro-2H-pyran → (2-Tetrahydropyranyl)oxynorbornyl alcohol

HRID 53857ノート

反応式

HRID 53857 の反応式
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[CH:7]12[CH2:13][CH:10]([CH2:11][CH2:12]1)[CH:9](O)[CH:8]2[OH:15].C(=O)([O-])[O-:17].[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>S(=O)(=O)(O)O.O1CCCC1>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:15][CH:8]1[CH2:9][CH:10]2[CH2:13][C:7]1([OH:17])[CH2:12][CH2:11]2

参加物

7

反応物 4

HCID 80803,4-dihydro-2H-pyranHCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 85735Bicyclo[2.2.1]heptane-2,3-diol

生成物 1

HCID 19960678(2-Tetrahydropyranyl)oxynorbornyl alcohol収率 19%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Into a 200 ml flask having four openings and equipped with a thermometer, a tube for introducing nitrogen gas into the flask, and a reflux tube were put 10.0 grams (0.11 mol) of 3,4-dihydro-2H-pyran, 12.8 grams (100 mmol) of norbornane-2,3-diol and 50 ml of dry tetrahydrofuran. Then, they were stirred. Then, five drops of thick sulfuric acid were added. Thereafter, the mixture was allowed to stand at a room temperature for 24 hours. After the mixture was cooled down to room temperature, 3 grams of solid sodium carbonate and 10 grams of anhydrous sodium sulfate were added to the mixture. Then, the mixture was stirred for 2 hours and filtrated. The gathered filtration was disposed with 0.2 grams of hydrogenated calcium. The residue obtained by removing excessive dihydropyran by means of a rotary evaporator under reduced pressure was refined through a silica gel column, in which ethyl acetate/n-hexane was used as an elution solvent, to thereby obtain 4.0 grams of (2-tetrahydropyranyl)oxynorbornyl alcohol. The yield was 19%. The obtained (2-tetrahydropyranyl)oxynorbornyl alcohol was oily.

後処理

  1. customInto a 200 ml flask having
  2. customfour openings and equipped with a thermometer, a tube
  3. additionfor introducing nitrogen gas into the flask, and a reflux tube
  4. stirringThen, the mixture was stirred for 2 hours
  5. filtrationfiltrated
  6. filtrationThe gathered filtration
  7. customThe residue obtained
  8. customby removing excessive dihydropyran
  9. customby means of a rotary evaporator under reduced pressure

出典と根拠

ORDレコード
ord-a52eac8a936f40898ece23a51d8827c4
出典データセット
uspto-grants-1997_04
特許番号
US05621019

反応ノート

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