Hydrochloric Acid → HCID 15161042, compound

HRID 1535055Notes

Reaction equation

HRID 1535055 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:11][CH2:12][CH2:13][C:14]1[C:30]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:29][C:17]2[CH2:18][CH:19]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][C:16]=2[CH:15]=1.Cl>CN(C)C=O>[CH2:32]([O:31][C:30]1[C:14]([CH2:13][CH2:12][CH2:11][O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:15][C:16]2[O:20][CH:19]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18][C:17]=2[CH:29]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 24758Sodium hydrideHCID 15161041HCID 15161041, compound

Product 1

HCID 15161042HCID 15161042, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Dry phenol (14 gm, 152 mmoles) was added to 50% sodium hydride dispersion (7 gm; 145 mmoles) in dimethylformamide (200 mL) under nitrogen atmosphere. After stirring for 30 minutes, a solution of 6-(3-bromopropyl)-5-benzyloxy-2-(2-phenylethyl)-2,3-dihydrobenzofuran, E88, (8.7 gm; 16.9 mmoles) in dimethylformamide (25 mL). The mixture was stirred at room temperature for 3 hours, poured into excess 1N hydrochloric acid and extracted with diethylether. The ether layer was washed with 1N sodium hydroxide twice, dried (MgSO4), filtered and concentrated in vacuo. The residue was chromatographed on silica gel using 5% ethyl acetate in hexane to yield 6.3 g (82%) of 5-benzyloxy-2-(2-phenylethyl)-6-(3-phenoxypropyl)-2,3-dihydrobenzofuran, E38, as an oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. extractionextracted with diethylether
  3. washThe ether layer was washed with 1N sodium hydroxide twice
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel using 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c1091663e16249309ec094ff40358767
Source dataset
uspto-grants-1992_02
Patent number
US05091533

Reaction notes

Loading…