Potassium Carbonate → HCID 25130206, compound

HRID 2076947Notes

Reaction equation

HRID 2076947 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[C@H:19]([CH2:20][OH:21])[CH2:18][CH2:17][C:12]2(OCC[O:13]2)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.O.CO>[CH2:1]([O:8][CH2:9][C@H:10]1[C@H:19]([CH2:20][OH:21])[CH2:18][CH2:17][C:12](=[O:13])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 25130205HCID 25130205, compound

Product 1

HCID 25130206HCID 25130206, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A solution composed of {(7R,8R)-7-[(benzyloxy)methyl]-1,4-dioxaspiro[4.5]dec-8-yl}methanol (33.6 g, 115 mmol) in a mixture of acetic acid (220 mL) and water (80 mL) was heated at 85° C. for 2 h. The solvents were removed by rotary evaporation under reduced pressure and the residue was partitioned between water and ethyl acetate. The aqueous phase was extracted with an additional portion of ethyl acetate and the combined organics were washed with saturated aqueous NaHCO3 and NaCl solutions, and dried over a mixture of Na2SO4 and MgSO4. Concentration in vacuo afforded a yellow syrup that was taken up in methanol (250 mL) and treated with K2CO3 (20 g, 150 mmol) with stirring at rt for 30 min. The methanol was then evaporated and the residue was taken up in ethyl acetate and washed with water, saturated aqueous NaCl solution, and dried a mixture of Na2SO4 and MgSO4. Concentration in vacuo provided (3R,4R)-3-[(benzyloxy)methyl]-4-(hydroxymethyl)cyclohexanone as a thick, yellow syrup. 1H NMR (500 MHz, d6-acetone) δ 7.36 (4H, m), 7.30 (1H, m), 4.56-4.50 (2H, m), 3.70 (1H, m), 3.66-3.60 (2H, m), 3.56 (1H, dd, J= 5.4, 9.3 Hz), 3.54-3.48 (1H, dd, J= 4.0, 9.3 Hz), 2.44-2.26 (4H, m), 2.13-2.07 (2H, m), 1.91 (1H, m), 1.67 (1H, m).

Workup

  1. customThe solvents were removed by rotary evaporation under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous phase was extracted with an additional portion of ethyl acetate
  4. washthe combined organics were washed with saturated aqueous NaHCO3 and NaCl solutions
  5. dry with materialdried over a mixture of Na2SO4 and MgSO4
  6. concentrationConcentration in vacuo
  7. customafforded a yellow syrup that
  8. customThe methanol was then evaporated
  9. washwashed with water, saturated aqueous NaCl solution
  10. customdried
  11. additiona mixture of Na2SO4 and MgSO4
  12. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-a2cdb866ab454471b2336b8f8cc38d4c
Source dataset
uspto-grants-2011_04
Patent number
US07928091B2

Reaction notes

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