Dichloromethane → 4,4-Dimethyl-7-(3-methyl-2-octyl)-9-[4-(morpholino)butyryloxy]-1,2,3,4-tetrahydrocyclopenta[c] [l] benzopyran hydrochloride

HRID 267336ノート

反応式

HRID 267336 の反応式
[CH3:1][C:2]1([CH3:25])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([OH:24])=[CH:12][C:13]([CH:15]([CH:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:16])=[CH:14][C:4]=2[O:3]1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[O:42]1[CH2:47][CH2:46][N:45]([CH2:48][CH2:49][CH2:50][C:51](O)=[O:52])[CH2:44][CH2:43]1.C(Cl)[Cl:55]>CO.C(Cl)(Cl)Cl>[ClH:55].[CH3:25][C:2]1([CH3:1])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([O:24][C:51](=[O:52])[CH2:50][CH2:49][CH2:48][N:45]3[CH2:44][CH2:43][O:42][CH2:47][CH2:46]3)=[CH:12][C:13]([CH:15]([CH:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:16])=[CH:14][C:4]=2[O:3]1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 215348Cyclopenta(c)(1)benzopyran-9-ol, 1,2,3,4-tetrahydro-4,4-dimethyl-7-(1,2-dimethylheptyl)-HCID 127337464-Morpholin-4-Yl-Butyric Acid Hydrochloride

生成物 1

HCID 681364364,4-Dimethyl-7-(3-methyl-2-octyl)-9-[4-(morpholino)butyryloxy]-1,2,3,4-tetrahydrocyclopenta[c] [l] benzopyran hydrochloride

試薬・触媒・溶媒 1

HCID 21584188Chloroform methanol溶媒

実験手順

6.4 g. (18.7 mmole) of 4,4-Dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-1,2,3,4-tetrahydrocyclopenta[ c][1] benzopyran, 4.33 g. (21.0 mmoles) of dicyclohexylcarbodiimide and 4.26 g. (20.3 mmoles) of γ-morpholinobutyric acid hydrochloride were combined with 325 ml. of methylene chloride and stirred at room temperature for a total of 24 hours. The insoluble by-product of dicyclohexylurea was separated by filtration and the methylene chloride was removed using a rotary evaporator. The brown viscous residue was dissolved in about 100 ml. of benzene and the benzene solution was filtered to remove a small amount of insoluble material. The benzene was removed using a rotary evaporator and the remaining residue was triturated with approximately 250 ml. of ether. The solid which formed was filtered, washed with ether and dried to give 8.6 g. of beige solid. The material was crystallized from benzene/ether to give 3.5 g. of product as a colorless solid, m.p. 151°-153°C. The material was pure by thin layer chromatography (10% MeOH/CHCl3); the infrared and nuclear magnetic resonance spectra were in agreement with the proposed structure. An additional 3.3 g. of somewhat impure material was recovered from the mother liquor.

後処理

  1. customThe insoluble by-product of dicyclohexylurea was separated by filtration
  2. customthe methylene chloride was removed
  3. customa rotary evaporator
  4. dissolutionThe brown viscous residue was dissolved in about 100 ml
  5. filtrationof benzene and the benzene solution was filtered
  6. customto remove a small amount of insoluble material
  7. customThe benzene was removed
  8. customa rotary evaporator
  9. customthe remaining residue was triturated with approximately 250 ml
  10. customThe solid which formed
  11. filtrationwas filtered
  12. washwashed with ether
  13. customdried
  14. customto give 8.6 g
  15. customThe material was crystallized from benzene/ether
  16. customto give 3.5 g
  17. customof somewhat impure material was recovered from the mother liquor

出典と根拠

ORDレコード
ord-f8285fb9271d4300b0b0b3e173429017
出典データセット
uspto-grants-1976_03
特許番号
US03941782

反応ノート

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