Benzoyl chloride → Cholestanol benzoate

HRID 1721303ノート

反応式

HRID 1721303 の反応式
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:28])[CH2:14][CH2:15][CH2:16]/[C:17](=[CH:18]\[CH:19]=[C:20]3\[CH2:21][C@@H:22]([OH:27])[CH2:23][CH2:24][C:25]\3=[CH2:26])/[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>N1C=CC=CC=1>[C:29]([O:27][C@H:22]1[CH2:23][CH2:24][C@@:25]2([CH3:26])[C@@H:20]([CH2:19][CH2:18][C@@H:17]3[C@@H:16]2[CH2:15][CH2:14][C@@:13]2([CH3:28])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C@H:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:7])[CH3:8])[CH2:21]1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

参加物

4

反応物 2

HCID 7412Benzoyl chlorideHCID 5280795Vitamin D3

生成物 1

HCID 251110Cholestanol benzoate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of 7-dehydrocholesterol (1, 50.0 g, 0.13 mol; Aldrich Chemical Co.) dissolved in dry pyridine (120 mL) was added, with stirring, benzoyl chloride (28 mL, 34.1 g, 0.24 mol). After the addition, the reaction mixture was heated at reflux for 5 min and was then left at ambient temperature for 20 min. The reaction mixture was poured with stirring into ice water (1.5 L). The precipitate was allowed to rest for 1 h and was then taken up on a filter and washed successively with water (350 mL), 5% sodium bicarbonate (200 mL), water (350 mL) and finally acetone (5×25 mL). The crude material was air dried and subsequently recrystallized. The crude material was dissolved in hot chloroform (100 mL) and to this solution was added acetone (250 mL). The flask was left at ambient temperature and then at -20° C. overnight. The crystalline material was collected by filtration, and then washed with a small amount of acetone. Total yield compound 2 after drying, 58.3 g (92%). Melting point and spectral data agree with previous reported values (Wilson et al., J. Org. Chem. 53:1713 (1988)).

後処理

  1. additionwas added
  2. additionAfter the addition
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 5 min
  5. additionThe reaction mixture was poured
  6. waitto rest for 1 h
  7. filtrationa filter
  8. washwashed successively with water (350 mL), 5% sodium bicarbonate (200 mL), water (350 mL) and finally acetone (5×25 mL)
  9. customdried
  10. customsubsequently recrystallized
  11. dissolutionThe crude material was dissolved in hot chloroform (100 mL) and to this solution
  12. additionwas added acetone (250 mL)
  13. waitThe flask was left at ambient temperature
  14. customat -20° C.
  15. customovernight
  16. filtrationThe crystalline material was collected by filtration
  17. washwashed with a small amount of acetone
  18. dry with materialTotal yield compound 2 after drying

出典と根拠

ORDレコード
ord-e8c5a215067448beaaf13a41b85e2445
出典データセット
uspto-grants-1996_04
特許番号
US05510340

反応ノート

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