Citric Acid → HCID 15161043, compound

HRID 1535050Notes

Reaction equation

HRID 1535050 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].Br[CH2:13][CH2:14][CH2:15][C:16]1[C:32]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:31][C:19]2[CH2:20][CH:21]([CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:18]=2[CH:17]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:13][CH2:14][CH2:15][C:16]2[C:32]([O:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[CH:31][C:19]3[CH2:20][CH:21]([CH2:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[O:22][C:18]=3[CH:17]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 130194-CyanophenolHCID 24758Sodium hydrideHCID 15161041HCID 15161041, compound

Product 1

HCID 15161043HCID 15161043, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-cyanophenol (1.07 gm, 9 mmoles) was added in one portion to 50% sodium hydride dispersion (435 mgs; 9 mmoles) in dimethylformamide (30 mL) under nitrogen atmosphere. After stirring for 30 minutes, a solution of 6-(3-bromopropyl)-5-benzyloxy-2-(2-phenylethyl)-2,3-dihydrobenzofuran, E88, (1 gm, 2.2 mmoles) in dimethylformamide (5 mL) was added. The mixture was stirred at room temperature for 18 hours. The mixture was poured into excess 20% citric acid solution and extracted with diethyl ether. The ether layer was backwashed with water, dried (MgSO4), filtered and concentrated in vacuo. The residue was chromatographed in silica gel using 15% ethylacetate in hexane as eluent to yield 1.06 gm (95%) as an oil of 6-[3-(4-cyanophenoxy)propyl]-5-benzyloxy-2(2-phenylethyl)-2,3-dihydrobenzofuran, E22, m.p. 154°-157° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. extractionextracted with diethyl ether
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed in silica gel using 15% ethylacetate in hexane as eluent

Sources & evidence

ORD record
ord-2ab4230fa3ae49a08e5154b04b6f105a
Source dataset
uspto-grants-1992_02
Patent number
US05091533

Reaction notes

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