Benzyl iodide → HCID 54538919, compound

HRID 846473Notes

Reaction equation

HRID 846473 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1[C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:18]=[CH:17][C:16]=1[OH:28].[CH2:29](I)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[CH2:29]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1[C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:18]=[CH:17][C:16]=1[OH:28])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 12098Benzyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21734064HCID 21734064, compound

Product 1

HCID 54538919HCID 54538919, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1 ml of a DMF solution containing 55.5 mg (0.1438 mmol) of 2,2'-dihydroxy-5,5'-bis (2-ethoxycarbonylethyl) biphenyl and 21.82 μl (0.1798 mmol) of benzyl iodide, there was added 27.43 μl (0.1798 mmol) of DBU and the resulting mixture was agitated for 4.5 hours at room temperature. After the solvent in the reaction mixture was evaporated off under reduced pressure, the evaporated residue was dissolved in chloroform. This solution was washed with dilute hydrochloric acid, water and aqueous sodium chloride solution in this sequence and was dried by adding anhydrous sodium sulfate. The residue obtained after the solvent had been evaporated off was purified by silica gel column chromatography (with 5 g of WAKO-gel C-200, eluent: toluene and toluene/ethyl acetate of 50/1) to obtain 52.8 mg (0.111 mmol, 77%) of 2-benzyloxy-2'-hydroxy-5,5'-bis (2-ethyoxycarbonylethyl) biphenyl as an oily product. 1H-NMR (CDCl3) δ (ppm): 1.23 (6H, t, 2CH3), 2.5-2.8 (4H, m, 2CH2), 2.8-3.1 (4H, m, 2CH 2), 4.13 (4H, q, 2CH2), 5.06 (2H, s, CH2), 6.27 (1H, s, OH), 6.8-7.4 (11H, m, arom-H) MS (FAB): 475 (M-H)-

Workup

  1. customAfter the solvent in the reaction mixture was evaporated off under reduced pressure
  2. dissolutionthe evaporated residue was dissolved in chloroform
  3. washThis solution was washed with dilute hydrochloric acid, water and aqueous sodium chloride solution in this sequence
  4. customwas dried
  5. additionby adding anhydrous sodium sulfate
  6. customThe residue obtained after the solvent
  7. customhad been evaporated off
  8. customwas purified by silica gel column chromatography (with 5 g of WAKO-gel C-200, eluent: toluene and toluene/ethyl acetate of 50/1)

Sources & evidence

ORD record
ord-bd2407b4a85b478b8191a42fd45da4f8
Source dataset
uspto-grants-1992_08
Patent number
US05136090

Reaction notes

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