Hydrochloric Acid → HCID 19908827, compound

HRID 1535056Notes

Reaction equation

HRID 1535056 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][C:21]1[C:37]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:36][C:24]2[CH2:25][CH:26]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:27][C:23]=2[CH:22]=1.Cl>CN(C)C=O>[CH3:12][O:11][C:9](=[O:10])[C:8]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:18][CH2:19][CH2:20][C:21]2[C:37]([O:38][CH2:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[CH:36][C:24]3[CH2:25][CH:26]([CH2:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[O:27][C:23]=3[CH:22]=2)=[CH:7][CH:6]=1)([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 14868251HCID 14868251, compoundHCID 15161041HCID 15161041, compound

Product 1

HCID 19908827HCID 19908827, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of methyl 2-(4-hydroxyphenyl)-2-methylpropionate (0.81 g; 4.19 mmol) in dry diemthylformamide (8 mL) was added sodium hydride (192 mg, 4 mmol) as a 50% dispersion in oil. The mixture was stirred at room temperature for 30 minutes. A solution of 6-(3-bromopropyl)-5-benzyloxy-2-(2-phenylethyl)-2,3-dihydrobenzofuran, E88, in dry dimethylformamide (2 mL) was added. The resulting mixture was stirred at room temperature for 20 hours. The mixture was poured into cold dilute HCl (1N, 25 mL) and extracted twice with ethylacetate (50 mL). The combined organic extracts were washed with 1N HCl (25 ml×2) and brine (25 mL), dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel to give 500 mg (87% yield) methyl-2-[4-[3-[2,3-dihydro-5-benzyloxy-2-(2-phenylethyl)benzofuran-6-yl]propoxy]phenyl]- 2-methylpropanoate, E42.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 20 hours
  2. extractionextracted twice with ethylacetate (50 mL)
  3. washThe combined organic extracts were washed with 1N HCl (25 ml×2) and brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-6f4f56a234ee4daeaf4e7135dd40bcdd
Source dataset
uspto-grants-1992_02
Patent number
US05091533

Reaction notes

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