Tetrahydrofuran → HCID 10766034, compound

HRID 1650222Notes

Reaction equation

HRID 1650222 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)=[C:6]2[C:11]=1[C:10](=[O:12])[C:9]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:8][CH2:7]2.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)=[C:6]2[C:11]=1[CH:10]([OH:12])[C:9]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:8][CH2:7]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 10575517HCID 10575517, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10766034HCID 10766034, compoundYield 78.5%

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). mp: 142.5°-143.5° C. IR (CHCl3) 3600, 3330, 2930, 2860, 1620, 1600, 1580, 1505, 1460, 1290, 1250, 1205, 1090, 820 cm-1. NMR (CDCl3, δ): 0.88 (3H, t, J=6 Hz) J=6 Hz), 1.05-2.05 (15H, m), 2.40-2.70 (1H, m), 2.98 (1H, dd, J=18, 6 Hz), 4.61 (1H, s), 5.37 (2H, s), 6.79 (1H, d, J=8 Hz), 7.18 (1H, d, J=8 Hz), 7.57 (1H, t, J=8 Hz), 7.66 (1H, d, J= 8 Hz), 7.75 (1H, t, J=8 Hz), 7.85 (1H, d, J=8 Hz), 8.08 (1H, d, J=8 Hz), 8.21 (1H, d, J=8 Hz).

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-bb891d57a61f4a489fd52d63589dd53f
Source dataset
uspto-grants-1990_05
Patent number
US04923881

Reaction notes

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