6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo(c)chromen-1-ol → 1-[4-(Morpholino)butyryloxy]-3-n-pentyl-6,6,9-trimethyl-10a,6a,7,8-tetrahydrodibenzo[b,d]pyran hydrobromide

HRID 2398886ノート

反応式

HRID 2398886 の反応式
[OH:1][C:2]1[C:11]2[CH:10]3[CH:12]=[C:13]([CH3:16])[CH2:14][CH2:15][CH:9]3[C:8]([CH3:18])([CH3:17])[O:7][C:6]=2[CH:5]=[C:4]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:3]=1.[BrH:24].[O:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][C:34](O)=[O:35])[CH2:27][CH2:26]1.C1(N=C=NC2CCCCC2)CCCCC1.C(Cl)Cl>CO.C(Cl)(Cl)Cl>[BrH:24].[O:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][C:34]([O:1][C:2]2[C:11]3[CH:10]4[CH:12]=[C:13]([CH3:16])[CH2:14][CH2:15][CH:9]4[C:8]([CH3:17])([CH3:18])[O:7][C:6]=3[CH:5]=[C:4]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:3]=2)=[O:35])[CH2:27][CH2:26]1

参加物

6

反応物 4

HCID 29786,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo(c)chromen-1-olHCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 68121683gamma-Morpholinobutyric acid hydrobromide

生成物 1

HCID 214339031-[4-(Morpholino)butyryloxy]-3-n-pentyl-6,6,9-trimethyl-10a,6a,7,8-tetrahydrodibenzo[b,d]pyran hydrobromide

試薬・触媒・溶媒 1

HCID 21584188Chloroform methanol溶媒

実験手順

3.54 g. (11.27 mmole) of 1-Hydroxy-3-n-pentyl-6,6,9-trimethyl-10a,6a,7,8-tetrahydrodibenzo[b,d]pyran, 2.86 g. (11.27 mmole) of γ-morpholinobutyric acid hydrobromide and 2.50 g. (12.12 mole) of dicyclohexylcarbodiimide were combined in 200 ml. of methylene chloride and stirred at room temperature for 24 hours. The reaction mixture was cooled and the by-product of dicyclohexylurea was removed by filtration. The volume of methylene chloride was reduced and 25 ml. of cyclohexane was added. The mixture was cooled and the small amount of solid which formed was removed by filtration. All solvents were removed on a rotary evaporator and the residue was dried in vacuo. The resulting foamy material was dissolved in a mixture of benzene and ether and placed in cold storage to yield 3.0 g. (50%) of product as colorless crystals, m.p. 103°-105°. The compound gave a Rf 0.5 in 5% MeOH/CHCl3. The infrared and nmr spectra are consistent with the proposed structure.

後処理

  1. temperatureThe reaction mixture was cooled
  2. customthe by-product of dicyclohexylurea was removed by filtration
  3. additionof cyclohexane was added
  4. temperatureThe mixture was cooled
  5. customthe small amount of solid which formed
  6. customwas removed by filtration
  7. customAll solvents were removed on a rotary evaporator
  8. customthe residue was dried in vacuo
  9. dissolutionThe resulting foamy material was dissolved in a mixture of benzene and ether
  10. customto yield 3.0 g

出典と根拠

ORDレコード
ord-5a52101fe3d541478c4958a144c2354d
出典データセット
uspto-grants-1977_05
特許番号
US04025630

反応ノート

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