Dimethylformamide → HCID 19822208, compound

HRID 1030401Notes

Reaction equation

HRID 1030401 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][O:6][C:7]1[C:8]([CH3:29])=[C:9]2[C:14](=[C:15]([CH3:18])[C:16]=1[CH3:17])[O:13][C:12]([CH2:27][OH:28])([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:11][CH2:10]2.CN(C)C=O.Cl[C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1>C1C=CC=CC=1>[CH3:3][O:4][CH2:5][O:6][C:7]1[C:8]([CH3:29])=[C:9]2[C:14](=[C:15]([CH3:18])[C:16]=1[CH3:17])[O:13][C:12]([CH2:27][O:28][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:11][CH2:10]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 74741-Chloro-4-nitrobenzeneHCID 24758Sodium hydrideHCID 19822214HCID 19822214, compound

Product 1

HCID 19822208HCID 19822208, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

0.38 g of a 55% w/w suspension of sodium hydride in mineral oil was added to a mixture of 3 g of 6-methoxymethoxy-5,7,8-trimethyl-2-octylchroman-2-ylmethanol (prepared as described in Preparation 13) and 25 ml of dimethylformamide under a nitrogen stream at room temperature, and the resulting mixture was heated for 2 hours at 50° C. A mixture of 1.4 g of p-chloronitrobenzene and 2 ml of benzene was then added dropwise, whilst ice-cooling, and the resulting mixture was heated for 2 hours at 50° C. The reaction mixture was then poured into ice-water and extracted with benzene. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography eluted with benzene, to give the title compound.

Workup

  1. additionwas then added dropwise, whilst ice-
  2. temperaturecooling
  3. temperaturethe resulting mixture was heated for 2 hours at 50° C
  4. extractionextracted with benzene
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe residue was purified by silica gel column chromatography
  9. washeluted with benzene

Sources & evidence

ORD record
ord-a42afdc18c1b4cb9881bdb0e34ca36f2
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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