5-Methoxybicyclo[4.2.0]octa-1,3,5-trien-7-one → Bicyclo[4.2.0]octa-1,3,5-trien-7-ol, 5-methoxy-

HRID 1872095Notes

Reaction equation

HRID 1872095 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[C:10]2[C:11](=[O:13])[CH2:12][C:9]=2[CH:8]=[CH:7][CH:6]=1>CO>[CH3:3][O:4][C:5]1[C:10]2[CH:11]([OH:13])[CH2:12][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 27527445-Methoxybicyclo[4.2.0]octa-1,3,5-trien-7-oneHCID 4311764Sodium borohydride

Product 1

HCID 10103323Bicyclo[4.2.0]octa-1,3,5-trien-7-ol, 5-methoxy-Yield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

13.21 g (0.35 mol) of sodium borohydride are added in small fractions to a solution, maintained at 0° C., of 42.8 g (0.29 mol) of 6-methoxybenzocyclobutan-1-one in 1.5 liters of methanol. The temperature is maintained at 0° C. for 2 hours. After returning to room temperature, the reaction mixture is evaporated to dryness and then taken up in water. The aqueous phase is extracted several times with ethyl acetate. The organic phases are combined, washed with brine, dried over MgSO4, filtered and evaporated to yield, after chromatography on silica, 29.2 g of the expected product in the form of a solid, the melting point of which is 71-73° C.

Workup

  1. customAfter returning to room temperature
  2. customthe reaction mixture is evaporated to dryness
  3. extractionThe aqueous phase is extracted several times with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto yield

Sources & evidence

ORD record
ord-eb337e61c1ce4e36971446a5f7b74f13
Source dataset
uspto-grants-2000_08
Patent number
US06107345

Reaction notes

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