Tetrahydrofuran → 2-(Benzyloxy)-3-(octadecyloxy)propan-1-OL

HRID 235698

反応式

HRID 235698 の反応式
[H-].[Na+].[CH2:3]([O:10][CH:11]([CH2:14][OH:15])[CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:16](I)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].O1CCCC1>CN(C)C=O.O>[CH2:3]([O:10][CH:11]([CH2:12][O:13][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])[CH2:14][OH:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 124021-IodooctadecaneHCID 24758Sodium hydrideHCID 2035672-(Phenylmethoxy)-1,3-propanediol

生成物 1

HCID 131165252-(Benzyloxy)-3-(octadecyloxy)propan-1-OL

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of about 26.07 g of washed about 50% sodium hydride in about 1000 ml of dimethylformamide was added about 90 g of 2-(benzyloxy)-1,3-propanediol with stirring under argon. An about 187.88 g portion of octadecyl iodide and about 150 ml of tetrahydrofuran were added and the thick mixture was stirred with a glass rod, and then with magnetic stirring for about 3 hours. Water was then added and the mixture was extracted with ether. The ether extract was washed with brine, dried and filtered through a pad of florisil. The solvent was removed and the residue chromatographed on florisil, eluting first with petroleum ether, then with about 10% ether in petroleum ether and finally eluting the product with about 30% ether in petroleum ether, giving about 73.3 g of the desired title compound as a waxy solid.

後処理

  1. stirringthe thick mixture was stirred with a glass rod
  2. stirringwith magnetic stirring for about 3 hours
  3. extractionthe mixture was extracted with ether
  4. extractionThe ether extract
  5. washwas washed with brine
  6. customdried
  7. filtrationfiltered through a pad of florisil
  8. customThe solvent was removed
  9. customthe residue chromatographed on florisil
  10. washeluting first with petroleum ether
  11. washwith about 10% ether in petroleum ether and finally eluting the product with about 30% ether in petroleum ether

出典と根拠

ORDレコード
ord-201115d14bf84535805a74c531cde2ed
出典データセット
uspto-grants-1987_02
特許番号
US04640913

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