Hexane → HCID 13575680, compound

HRID 465033Notes

Reaction equation

HRID 465033 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][CH:9]([CH2:11][OH:12])[O:10][C:6]=2[C:5]([N+:13]([O-:15])=[O:14])=[CH:4][C:3]=1[CH3:16].[CH3:17]CCCCC>O1CCCC1>[Cl:1][C:2]1[C:7]2[CH2:8][CH:9]([CH2:11][O:12][CH3:17])[O:10][C:6]=2[C:5]([N+:13]([O-:15])=[O:14])=[CH:4][C:3]=1[CH3:16]

Participants

4

Reactant 2

HCID 8058HexaneHCID 13575679HCID 13575679, compound

Product 1

HCID 13575680HCID 13575680, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the 7C in 200 ml of tetrahydrofuran (THF) was added slowly drop-by-drop to a stirred mixture of 5.7 g of freshly hexane-washed sodium hydride in 100 ml of THF, under nitrogen, at 25°-28° C. After gas ceased to envolve, 42.6 g of methyl iodide was added drop-by-drop over 5 minutes. The mixture was stirred for 18 hours at room temperature, mixed with ice water, and the resulting mixture was extracted with methylene chloride. The extract was washed with cold water, dried (MgSO4) and the solvent was evaporated. The residue was chromatographed over silica gel, using a 1:24 mixture of THF and hexane as eluent. The first fraction that was collected was recrystallized from ether to give 4-chloro-2,3-dihydro-2-(methoxymethyl)-5-methyl-7-nitrobenzofuran (7D), as a tan solid, m.p.: 117°-119° C.

Workup

  1. washwashed sodium hydride in 100 ml of THF
  2. customat 25°-28° C
  3. addition42.6 g of methyl iodide was added drop-by-drop over 5 minutes
  4. additionmixed with ice water
  5. extractionthe resulting mixture was extracted with methylene chloride
  6. washThe extract was washed with cold water
  7. dry with materialdried (MgSO4)
  8. customthe solvent was evaporated
  9. customThe residue was chromatographed over silica gel
  10. additiona 1:24 mixture of THF and hexane as eluent
  11. customThe first fraction that was collected
  12. customwas recrystallized from ether

Sources & evidence

ORD record
ord-2380579e7df94702881f4ee61b941b57
Source dataset
uspto-grants-1985_10
Patent number
US04550121

Reaction notes

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