Tetrahydrofuran → HCID 178419637, compound

HRID 1706165Notes

Reaction equation

HRID 1706165 reaction equation
[Mg:1].O1CCCCC1OC1C=CC([Br:15])=CC=1.CN(C)[CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24](C(C(CC)C2C=CC=CC=2)=O)=[CH:23][CH:22]=1.[Cl-].[NH4+].[O:41]1C[CH2:44][CH2:43][CH2:42]1>CCOCC>[O:41]1[CH2:42][CH2:43][CH2:44][CH2:18][CH:19]1[O:20][C:21]1[CH:22]=[CH:23][C:24]([Mg:1][Br:15])=[CH:25][CH:26]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 46464362-(4-Bromophenoxy)tetrahydro-2H-pyranHCID 5462224MagnesiumHCID 98615461-(4-(2-Dimethylamino)-2-ethoxyphenyl butanone

Product 1

HCID 178419637HCID 178419637, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of p-(2-tetrahydropyranyloxy)phenyl magnesium bromide was prepared in the usual manner from magnesium (1.65 g.) and p-(2-tetrahydropyranyloxy)phenyl bromide (8.48 g.) in a mixture of dry ether (30 ml.) and dry tetrahydrofuran (30 ml.). To this solution was added a solution of 4-(β-dimethylaminoethoxy)-α-ethyldesoxybenzoin (9.33 g.) in ether (50 ml.). The mixture was heated under reflux for 2 hours, cooled and decomposed by the addition of saturated ammonium chloride solution. The organic layer was separated, and the aqueous layer was extracted with ether. The extract was combined with the organic layer, dried and evaporated to give 1-(p-β-dimethylaminoethoxyphenyl)-1-[p-(2-tetrahydropyranyloxy)phenyl]-2-phenylbutan-1-ol as an oil used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ether
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-d66e5f1652c04cb6b653c87c6860f1c8
Source dataset
uspto-grants-1980_06
Patent number
US04206234

Reaction notes

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