Methanol → HCID 59283859, compound

HRID 1641999Notes

Reaction equation

HRID 1641999 reaction equation
C([O:4][C:5]1[C:14]([CH3:15])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[CH2:16][CH:17]=[CH2:18])(=O)C.[CH3:19][OH:20]>>[OH:4][C:5]1[C:14]([CH3:15])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[CH2:16][CH:17]([O:20][CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 887MethanolHCID 59283848HCID 59283848, compound

Product 1

HCID 59283859HCID 59283859, compound

Procedure

A solution of methyl 4-acetoxy-3-allyl-5-methylbenzoate (175 mg, 0.75 mmol) in methanol (2 mL) was cooled in an ice-bath under a nitrogen atmosphere and treated with mercuric trifluoroacetate (322 mg, 1 equivalent). The reaction was stirred in the ice-bath for one hour by which time TLC analysis showed complete consumption of staring material. The reaction was then treated with 1 mL of 3 N NaOH and after vigorous stirring for 2 minutes, a solution of sodium borohydride (0.5 M, 1 mL) in 3 N NaOH was added. The back suspension was stirred for 5 minutes in the ice-bath and then ethyl acetate (25 mL) was added. After stirring for an additional 5 minutes, the ethyl acetate solution was decanted and then washed twice with saturated aqueous ammonium chloride. It was then dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The crude product (141 mg, oil) was purified by preparative TLC on silica using 15% ethyl acetate/hexanes. Purified Yield=82 mg (˜50%), MALDI-TOF 239 obs.

Workup

  1. customconsumption of staring material
  2. additionThe reaction was then treated with 1 mL of 3 N NaOH
  3. additiona solution of sodium borohydride (0.5 M, 1 mL) in 3 N NaOH was added
  4. stirringThe back suspension was stirred for 5 minutes in the ice-bath
  5. additionethyl acetate (25 mL) was added
  6. stirringAfter stirring for an additional 5 minutes
  7. customthe ethyl acetate solution was decanted
  8. washwashed twice with saturated aqueous ammonium chloride
  9. dry with materialIt was then dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated to dryness
  12. customThe crude product (141 mg, oil) was purified by preparative TLC on silica using 15% ethyl acetate/hexanes
  13. customPurified Yield=82 mg (˜50%), MALDI-TOF 239 obs

Sources & evidence

ORD record
ord-48d43689cba048cb85d2471209c8bd22
Source dataset
uspto-grants-2012_02
Patent number
US08119422B2

Reaction notes

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