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

HRID 1586680Notes

Reaction equation

HRID 1586680 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-89832e30c95f4598be58f98679bca1b8
Source dataset
uspto-grants-1993_06
Patent number
US05215975

Reaction notes

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