Dicyclohexylcarbodiimide → 1-[2-Methyl-4-(morpholino)butyryloxy]-3-(3-methyl-2-octyl)-7,8,9,10-tetrahydro-6,6,10-trimethyl-6H-dibenzo[b,d]pyran

HRID 267354Notes

Reaction equation

HRID 267354 reaction equation
[OH:1][C:2]1[C:11]2[C:10]3[CH:12]([CH3:16])[CH2:13][CH2:14][CH2:15][C:9]=3[C:8]([CH3:18])([CH3:17])[O:7][C:6]=2[CH:5]=[C:4]([CH:19]([CH:21]([CH3:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:20])[CH:3]=1.Cl.[CH3:29][CH:30]([CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1)[C:31](O)=[O:32].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:29][CH:30]([CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1)[C:31]([O:1][C:2]1[C:11]2[C:10]3[CH:12]([CH3:16])[CH2:13][CH2:14][CH2:15][C:9]=3[C:8]([CH3:17])([CH3:18])[O:7][C:6]=2[CH:5]=[C:4]([CH:19]([CH:21]([CH3:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:20])[CH:3]=1)=[O:32]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 30450106H-Dibenzo(b,d)pyran-1-ol, 7,8,9,10-tetrahydro-3-(1,2-dimethylheptyl)-6,6,10-trimethyl-HCID 681179462-Methyl-4-morpholinobutyric acid hydrochloride

Product 1

HCID 215555091-[2-Methyl-4-(morpholino)butyryloxy]-3-(3-methyl-2-octyl)-7,8,9,10-tetrahydro-6,6,10-trimethyl-6H-dibenzo[b,d]pyran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.2 g. (3.24 mmole) of 1-hydroxy-3-(3-methyl-2-octyl)-7,8,9,10-tetrahydro-6,6,10-trimethyl-6H-dibenzo[b,d]pyran, 0.73 g. (3.24 mmole) of 2-methyl-4-morpholinobutyric acid hydrochloride, 0.71 g. (3.46 mmole) of dicyclohexylcarbodiimide and 50 ml. of methylene chloride was stirred at room temperature for 16 hrs. The reaction mixture was cooled and the byproduct of dicyclohexylurea was removed by filtration. The solvent was evaporated to give a foamy residue which was chromatographed using activated magnesium silicate and methanol/chloroform solvent mixtures. The fractions were monitored by thin layer chromatography and the desired material was obtained from the 2% methanol/chloroform fractions. The appropriate fractions were collected and evaporated to give 0.9 g. (51%) of light purple gum.

Workup

  1. additionA mixture of 1.2 g
  2. temperatureThe reaction mixture was cooled
  3. customthe byproduct of dicyclohexylurea was removed by filtration
  4. customThe solvent was evaporated
  5. customto give a foamy residue which
  6. customwas chromatographed

Sources & evidence

ORD record
ord-54110bef6cc64793a286a8057f52a9a1
Source dataset
uspto-grants-1976_03
Patent number
US03941782

Reaction notes

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