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 267340노트

반응식

HRID 267340 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 21584188Chloroform methanol용매

실험 절차

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 evaporation 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°C. The compound gave a Rf 0.5 in 5% MeOH/CHCl3. The infrared and nuclear magnetic resonance spectra were consistent with the proposed structure.

후처리

  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 evaporation
  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

출처 및 근거

ORD 기록
ord-3aeec7074d55418ea1983fa2bc591e43
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03941782

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