Tetrahydrofuran → 6-[(8-Methoxy-4,8-dimethylnonan-2-yl)oxy]-2,3-dihydro-1-benzofuran

HRID 1414820Notes

Reaction equation

HRID 1414820 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[CH:3]=1.O1CCCC1.[H-].[Na+].C1(C)C=CC(S(O[CH:28]([CH3:40])[CH2:29][CH:30]([CH3:39])[CH2:31][CH2:32][CH2:33][C:34]([O:37][CH3:38])([CH3:36])[CH3:35])(=O)=O)=CC=1>CN(C)P(=O)(N(C)C)N(C)C>[CH3:38][O:37][C:34]([CH3:35])([CH3:36])[CH2:33][CH2:32][CH2:31][CH:30]([CH3:39])[CH2:29][CH:28]([O:1][C:2]1[CH:10]=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[CH:3]=1)[CH3:40]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 122365402,3-Dihydro-1-benzofuran-6-olHCID 21485174HCID 21485174, compound

Product 1

HCID 214852106-[(8-Methoxy-4,8-dimethylnonan-2-yl)oxy]-2,3-dihydro-1-benzofuran

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 2.7 g. of 6-hydroxy-2,3-dihydrobenzofuran in 10 ml. of absolute tetrahydrofuran is allowed to drop at 0° C. and while stirring into a suspension, cooled in ice, of 0.5 g. of sodium hydride in 5 ml. of absolute tetrahydrofuran. The mixture is stirred for 2 hours (during which time it is allowed to warm up to room temperature), again cooled to 0° C. and added dropwise to a solution of 7.13 g. of 7-methoxy-1,3,7-trimethyloctyl p-toluenesulfonate in 10 ml. of absolute tetrahydrofuran. The mixture is then diluted with 4 ml. of absolute hexamethylphosphoric acid triamide and stirred for 20 hours at room temperature. The mixture is then poured onto ice-water, extracted three times with diethyl ether, the ether extracts are washed with water and saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated. By chromatography on silica gel with hexane/ethyl acetate (19:1 parts by volume) there is obtained pure 2,3-dihydro-6-[(7-methoxy-1,3,7-trimethyloctyl)-oxy]-benzofuran which is distilled in a bulb-tube at 145° C./0.03 mmHg; nD20 = 1.5046.

Workup

  1. customto drop at 0° C.
  2. temperaturecooled in ice, of 0.5 g
  3. stirringThe mixture is stirred for 2 hours (during which time it
  4. temperatureagain cooled to 0° C.
  5. additionadded dropwise to a solution of 7.13 g
  6. additionThe mixture is then diluted with 4 ml
  7. additionThe mixture is then poured onto ice-water
  8. extractionextracted three times with diethyl ether
  9. washthe ether extracts are washed with water and saturated aqueous sodium chloride solution
  10. dry with materialdried over sodium sulfate
  11. customevaporated

Sources & evidence

ORD record
ord-d3d53026d5d94c3f82497aeb879bcc29
Source dataset
uspto-grants-1977_01
Patent number
US04002647

Reaction notes

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