Dimethylformamide → 3-[[8-([1,1'-Biphenyl]-4-yloxy]octyl]oxy]-2-methoxy-1-propanol

HRID 35949Notes

Reaction equation

HRID 35949 reaction equation
[C:1]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH:18](O)[CH2:19][O:20]C(C2C=CC(OC)=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:3][CH:2]=1.CCCCCC.CN(C)[CH:57]=[O:58]>O1CCCC1>[C:1]1([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH:18]([O:58][CH3:57])[CH2:19][OH:20])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8058HexaneHCID 19939569HCID 19939569, compound

Product 1

HCID 677861083-[[8-([1,1'-Biphenyl]-4-yloxy]octyl]oxy]-2-methoxy-1-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7.6 g of 1-[[8-([1,1'-biphenyl]-4-yloxy)octyl]oxy]-3-[(4-methoxyphenyl)diphenylmethoxy]-2-propanol in 20 ml of dimethylformamide and 20 ml of tetrahydrofuran was added dropwise to a solution of 849 mg of hexane washed 50% sodium hydride in 50 ml of dimethylformamide containing 5.02 g of methyl iodide over 35 minutes under argon. The mixture was stirred overnight then ice was cautiously added followed by 300 ml of iced water. This mixture was extracted three times with ether, the extracts combined, washed with water, dried and evaporated. The residue was taken up in 65 ml of chloroform and 130 ml of methanol, heated to boiling, 8 g of Amberlite® IR-4B ion exchange resin added, stirred for 2 hours, filtered and evaporated. The residue was purified by chromatography, giving 1.27 g of 3-[[8-([1,1'-biphenyl]-4-yloxy]octyl]oxy]-2-methoxy- 1-propanol.

Workup

  1. washwashed 50% sodium hydride in 50 ml of dimethylformamide containing 5.02 g of methyl iodide over 35 minutes under argon
  2. additionice was cautiously added
  3. extractionThis mixture was extracted three times with ether
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. temperature130 ml of methanol, heated
  8. addition8 g of Amberlite® IR-4B ion exchange resin added
  9. stirringstirred for 2 hours
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-69cc414d883149e6adf38e0b512aaeec
Source dataset
uspto-grants-1995_05
Patent number
US05411983

Reaction notes

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