Tetrahydrofuran → 3-(6-Benzyloxynaphthalen-2-yl)pentan-3-ol

HRID 550201Notes

Reaction equation

HRID 550201 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=2)[CH:6]=1)=O.[CH2:23]([Mg]Br)[CH3:24].[CH2:27]1COC[CH2:28]1>>[CH2:16]([O:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([C:3]([OH:2])([CH2:23][CH3:24])[CH2:27][CH3:28])[CH:14]=[CH:13]2)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 199902746-Benzyloxynaphthalene-2-carboxylic acid methyl esterHCID 178418443HCID 178418443, compound

Product 1

HCID 578714103-(6-Benzyloxynaphthalen-2-yl)pentan-3-olYield 95%

Procedure

Cool 6-benzyloxynaphthalene-2-carboxylic acid methyl ester (5.75 g, 19.67 mmol) in THF (115 mL) to about 0° C. and treat the solution dropwise with ethyl magnesium bromide (23.0 mL, 69.0 mmol, 3.0 M in ether). Allow the reaction to warm to RT and stir it for 3 h. Quench with water and concentrate. Dissolve the crude residue in CH2CL2 (200 mL), wash twice with brine, dry over Na2SO4 and filter. Concentrate the filtrate to give the title compound as a yellow solid (6.0 g, 95%). MS (ES) m/e 321 (M+1).

Workup

  1. customthe reaction
  2. customQuench with water
  3. concentrationconcentrate
  4. dissolutionDissolve the crude residue in CH2CL2 (200 mL)
  5. washwash twice with brine
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-819b0ad5448347329669d73913925d87
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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