Acetic Acid → HCID 21468098, compound

HRID 1939741Notes

Reaction equation

HRID 1939741 reaction equation
[OH:1][CH:2]([C:8]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]2[C:10](=[C:11]([O:22][CH3:23])[CH:12]=[CH:13][C:14]=2[O:20][CH3:21])[C:9]=1[O:24][CH3:25])[CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6].C1CCC(N=C=NC2CCCCC2)CC1.ClCCl.[C:44](O)(=[O:46])[CH3:45]>CN(C)C1C=CN=CC=1.CCCCCC>[C:44]([O:1][CH:2]([C:8]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]2[C:10](=[C:11]([O:22][CH3:23])[CH:12]=[CH:13][C:14]=2[O:20][CH3:21])[C:9]=1[O:24][CH3:25])[CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6])(=[O:46])[CH3:45]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 14083905HCID 14083905, compound

Product 1

HCID 21468098HCID 21468098, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8058HexaneSolvent

Procedure

In a 25 ml two-neck flask 1 mmole of 2-(1-hydroxy-4-methylpentyl)-1,4,5,8-tetramethoxynaphthalene, 226 mg (1.1 mmole) of DCC and 30 mg (0.25 mmole) of 4-dimethylaminopyridine were introduced and then 3 ml of dry dichloromethane was added thereto. After adding 1 mmole of acetic acid at 0° C. under nitrogen gas, the reaction mixture was stirred for 30 minutes and then subsequently stirred at normal temperature for further 3 hours. To the reaction mixture was added 20 ml of n-hexane. The mixture was stirred for further 10 minutes and then filtered to remove the insoluble materials. The filtrate was dried over anhydrous magnesium sulfate to obtain a crude product. The crude product was purified by silica gel column chromatography (silica gel 2.5×20 cm) using the solvent condition which increases the amount of ethylacetate so that the n-hexane/ethylacetate ratio can vary from 20:1 to 5:1, to obtain the title compound as a pale yellow oil.

Workup

  1. stirringsubsequently stirred at normal temperature for further 3 hours
  2. stirringThe mixture was stirred for further 10 minutes
  3. filtrationfiltered
  4. customto remove the insoluble materials
  5. dry with materialThe filtrate was dried over anhydrous magnesium sulfate
  6. customto obtain a crude product
  7. customThe crude product was purified by silica gel column chromatography (silica gel 2.5×20 cm)
  8. temperatureincreases the amount of ethylacetate so that the n-hexane/ethylacetate ratio

Sources & evidence

ORD record
ord-755dbc4ad2564deb9e2159f8b029e889
Source dataset
uspto-grants-1997_12
Patent number
US05696276

Reaction notes

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