Magnesium → 1-(3-Benzyloxy-5-fluorophenyl)-2-methoxycyclopentanol

HRID 2226891Notes

Reaction equation

HRID 2226891 reaction equation
[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([Mg]Br)[CH:20]=[C:21]([F:23])[CH:22]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OC1C=C(Br)C=C(F)C=1)C1C=CC=CC=1.[Mg]>O1CCCC1>[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([C:4]2([OH:8])[CH2:5][CH2:6][CH2:7][CH:3]2[O:2][CH3:1])[CH:20]=[C:21]([F:23])[CH:22]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 5462224MagnesiumHCID 112545161-(Benzyloxy)-3-bromo-5-fluorobenzeneHCID 124766872-Methoxycyclopentan-1-oneHCID 178505958HCID 178505958, compound

Product 1

HCID 193879111-(3-Benzyloxy-5-fluorophenyl)-2-methoxycyclopentanolYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

After repetition of the above reaction, a solution of 2-methoxycyclopentanone (12.5 g) in tetrahydrofuran (10 ml) was added to a solution of 3-benzyloxy-5-fluorophenylmagnesium bromide [prepared by heating a mixture of 3-benzyloxy-5-fluorobromobenzene (31 g), magnesium powder (2.65 g) and tetrahydrofuran (20 ml) to 40° C. for 2 hours] and the mixture was stirred at ambient temperature for 2 hours. The mixture was evaporated and the residue was partitioned between diethyl ether and rarer, The organic layer was washed with water, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 9:1 v/v mixture of methylene chloride and diethyl ether as eluent. There was thus obtained, as a mixture of diastereoisomers, 1-(3-benzyloxy-5-fluorophenyl)-2-methoxycyclopentanol (21.7 g, 62%), as an oil.

Workup

  1. customAfter repetition of the above reaction
  2. customprepared
  3. temperatureby heating
  4. customThe mixture was evaporated
  5. customthe residue was partitioned between diethyl ether
  6. washrarer, The organic layer was washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by column chromatography
  10. additiona 9:1 v/v mixture of methylene chloride and diethyl ether as eluent

Sources & evidence

ORD record
ord-947056a75ecb49f1bd189474b822fd4d
Source dataset
uspto-grants-1994_09
Patent number
US05350754

Reaction notes

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