Trifluoroacetic acid → 15-Hydroxy-9-oxoprostanoic acid, ethyl ester

HRID 1448226Notes

Reaction equation

HRID 1448226 reaction equation
C([O:5][CH:6]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:7][CH2:8][C@@H:9]1[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:12](=[O:25])[CH2:11][CH2:10]1)(C)(C)C.FC(F)(F)C(O)=O>>[OH:5][CH:6]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:7][CH2:8][C@@H:9]1[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:12](=[O:25])[CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 8673293815-(Tert-butoxy)-9-oxoprostanoic acid, ethyl ester

Product 1

HCID 1859466215-Hydroxy-9-oxoprostanoic acid, ethyl ester

Procedure

A solution of 25 g. of 15-(tert-butoxy)-9-oxoprostanoic acid, ethyl ester in 100 ml. of trifluoroacetic acid is stirred in an ice bath for 1 hour and is then poured into 500 ml. of ice water and extracted several times with chloroform. The combined chloroform extracts are washed with saturated sodium bicarbonate solution, saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and taken to dryness. The resulting oil is dissolved in 200 ml. of 1N ammonium hydroxide in ethanol, kept at ambient temperature for 15 minutes, then taken to dryness. The residual oil is dissolved in chloroform and washed with 1N hydrochloric acid, saturated sodium chloride solution, dried and taken to dryness to give 21.7 g. (100%) of product as a yellow syrup. There is essentially no uv absorption; λmaxKBr 2.90, 5.75, 8.45 μ; nmr 2H quartet δ4.13 (OCH2 of ester), 1H broad singlet 3.63 (carbinolic proton), 3H triplet (CH3 of ester), and 3H distorted triplet 0.92 (terminal methyl); mass spectrum: m/e 368.

Workup

  1. additionis then poured into 500 ml
  2. extractionof ice water and extracted several times with chloroform
  3. washThe combined chloroform extracts are washed with saturated sodium bicarbonate solution, saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. dissolutionThe resulting oil is dissolved in 200 ml
  6. dissolutionThe residual oil is dissolved in chloroform
  7. washwashed with 1N hydrochloric acid, saturated sodium chloride solution
  8. customdried
  9. customto give 21.7 g
  10. customno uv absorption

Sources & evidence

ORD record
ord-0c4cfbede5ac4018a34afd60274f8eb8
Source dataset
uspto-grants-1979_12
Patent number
US04179574

Reaction notes

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