Acetic Acid → HCID 22145875, compound

HRID 993307Notes

Reaction equation

HRID 993307 reaction equation
O.[CH:2]1([O:7][C:8]2[C:13]([O:14][CH:15]([F:17])[F:16])=[CH:12][N:11]=[C:10](OC(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[C:38](O)(=[O:40])C>>[CH:2]1([O:7][C:8]2[C:13]([O:14][CH:15]([F:16])[F:17])=[CH:12][N:11]=[C:10]([CH2:38][OH:40])[CH:9]=2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 22145729HCID 22145729, compound

Product 1

HCID 22145875HCID 22145875, compound

Conditions

Temperature
60 °C

Procedure

Water (4 drops is added to a solution of 4-cyclopentyloxy-5-difluoromethoxy-2-trityloxypyridine (900 mg) in glacial acetic acid (20 mL) and the mixture heated at 60° C. for 18 hours. After cooling the mixture is evaporated to dryness and the residue partitioned between water and ethyl acetate. The organic phase is dried over magnesium sulphate and evaporated to give a pale yellow solid which is purified by flash chromatography (gradient elution using n-pentane/ethyl acetate 7:3 v/v to n-pentane/ethyl acetate 2:3 v/v on silica) to give 4-cyclopentyloxy-5-difluoromethoxy-2-hydroxymethylpyridine (250 mg) as a white solid, m.p. 85-6° C.

Workup

  1. temperatureAfter cooling the mixture
  2. customis evaporated to dryness
  3. customthe residue partitioned between water and ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customevaporated
  6. customto give a pale yellow solid which
  7. customis purified by flash chromatography (gradient elution using n-pentane/ethyl acetate 7:3 v/v to n-pentane/ethyl acetate 2:3 v/v on silica)

Sources & evidence

ORD record
ord-a23aa0f7987e413ab2f2d7662efc8045
Source dataset
uspto-grants-2002_10
Patent number
US06472412B1

Reaction notes

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