Tetrahydrofuran → HCID 10766034, compound

HRID 727818Notes

Reaction equation

HRID 727818 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][CH2:17][C:18]2=[O:23].O1[CH2:28][CH2:27][CH2:26][CH2:25]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-:35].[NH4+]>C(OCC)C>[Cl:35][C:20]1[CH:21]=[CH:22][C:13]([O:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[C:14]2[C:19]=1[CH:18]([OH:23])[C:17]([CH2:11][CH2:2][CH2:3][CH3:4])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:15]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 131716996HCID 131716996, compound

Product 1

HCID 10766034HCID 10766034, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 8-chloro-2,2-dibutyl-3,4-dihydro-(5(2-quinolylmethoxy)-1(2H)-naphthalenone (180 mg) in freshly distilled tetrahydrofuran (5 ml) was added lithium aluminum hydride (15 mg) with stirring in an ice bath under nitrogen and the mixture was stirred for minutes in an ice bath. To the mixture was carefully added aqueous saturated ammonium chloride solution (5 ml) in an ice bath, and then diethylether (10 ml) was added thereto. The separated aqueous layer was extracted two times with diethyl ether and the combined organic layers were washed with brine. The organic layer was dried over magnesium sulfate and concentrated in vacuo to give the oily residue which was crystallized from diisopropyl ether to yield 8-chloro-2,2-dibutyl-5-(2-quinolylmethoxy)-1,2,3,4-tetrahydro-1-naphthol (142 mg).

Workup

  1. stirringthe mixture was stirred for minutes in an ice bath
  2. extractionThe separated aqueous layer was extracted two times with diethyl ether
  3. washthe combined organic layers were washed with brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give the oily residue which
  7. customwas crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-4b529074a2d64b69bca12c576fb201e1
Source dataset
uspto-grants-1991_09
Patent number
US05045548

Reaction notes

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