Methane, dichloromethoxy- → HCID 23333166, compound

HRID 224438Notes

Reaction equation

HRID 224438 reaction equation
[CH:1]1([C:7]2[CH:15]=[CH:14][C:10]3[CH2:11][CH2:12][O:13][C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH:17]([O:19]C)Cl>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH:1]1([C:7]2[C:15]([CH2:17][OH:19])=[CH:14][C:10]3[CH2:11][CH2:12][O:13][C:9]=3[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 12878335HCID 12878335, compound

Product 1

HCID 23333166HCID 23333166, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

5 g of 6-Cyclohexyl-2,3-dihydro-benzofuran are dissolved in methylene chloride. 9.5 ml of TiCl4 are slowly added dropwise whilst cooling and stirring, followed by 2.9 g of dichloromethylmethylether in 10 ml of Ch2Cl2. The mixture is stirred for 5 hours at 22°, poured onto ice-water and extracted with ethyl acetate. The organic phase is washed with water, dried over Na2SO4 and reduced in volume. The residue is dissolved in tetrahydrofuran without further purification. An excess of NaBH4 is added and the mixture refluxed for 3 hours. Natural working of the mixture yields 6-cyclohexyl-2,3-dihydro-5-hydroxymethyl-benzofuran.

Workup

  1. temperaturewhilst cooling
  2. stirringThe mixture is stirred for 5 hours at 22°
  3. additionpoured onto ice-water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with water
  6. dry with materialdried over Na2SO4
  7. dissolutionThe residue is dissolved in tetrahydrofuran without further purification
  8. additionAn excess of NaBH4 is added
  9. temperaturethe mixture refluxed for 3 hours

Sources & evidence

ORD record
ord-479567be9922490cba97adb20ab3dc63
Source dataset
uspto-grants-1980_11
Patent number
US04232039

Reaction notes

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