Diethyl Ether → HCID 10131142, compound

HRID 1389147Notes

Reaction equation

HRID 1389147 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([CH2:14][CH2:15][C:16](=[O:18])[CH3:17])[CH:3]=1.[BH4-].[Na+].CCOCC>C(O)C>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([CH2:14][CH2:15][CH:16]([OH:18])[CH3:17])[CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 9859690HCID 9859690, compound

Product 1

HCID 10131142HCID 10131142, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(4-Fluoro-6-methoxy-2-naphthyl)butan-2-one (14.1 g) was dissolved in ethanol (200 ml) and sodium borohydride (6.7 g) was added to the stirred solution. After 1 hour ether (600 ml) was added and the solution was washed twice with brine, then with dilute hydrochloric acid and sodium hydrogen carbonate solution. After drying over anhydrous sodium sulphate the solvent was removed under reduced pressure. The oil obtained was chromatographed on silica gel (700 g) using an elution gradient from benzene to ether. The desired product was obtained as an oil. This was triturated with 60-80 petroleum ether to give the title compound as pale yellow crystals (5.65 g., 40%; m.p. 58°-60°).

Workup

  1. washthe solution was washed twice with brine
  2. dry with materialAfter drying over anhydrous sodium sulphate the solvent
  3. customwas removed under reduced pressure
  4. customThe oil obtained
  5. customwas chromatographed on silica gel (700 g)

Sources & evidence

ORD record
ord-c3b78237a1d346edbf890db995bc3934
Source dataset
uspto-grants-1981_01
Patent number
US04243682

Reaction notes

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