Acetic Acid → HCID 57202929, compound

HRID 1885557Notes

Reaction equation

HRID 1885557 reaction equation
C[Si](C)(C(C)(C)C)O[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C@@H:15]1[CH2:32][C:31]2[C@H:26]([CH2:27][CH2:28][C:29](=[O:33])[CH:30]=2)[C@@H:25]2[C@@H:16]1[C@H:17]1[C@@:21]([CH2:23][CH2:24]2)([CH3:22])[C:20](=[O:34])[CH2:19][CH2:18]1.[C:40]([OH:43])(=[O:42])[CH3:41].O.C(OC(=O)C)(=O)C>O1CCCC1.C(OCC)C.N1C=CC=CC=1>[C:40]([O:43][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C@@H:15]1[CH2:32][C:31]2[C@H:26]([CH2:27][CH2:28][C:29](=[O:33])[CH:30]=2)[C@@H:25]2[C@@H:16]1[C@H:17]1[C@@:21]([CH2:23][CH2:24]2)([CH3:22])[C:20](=[O:34])[CH2:19][CH2:18]1)(=[O:42])[CH3:41]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 571726537alpha-[11-(Dimethyl-tert-butyl-silyloxy)undecyl]-4-estrene-3,17-dione

Product 1

HCID 57202929HCID 57202929, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

28.3 g of 7α-[11-(dimethyl-tert-butylsilyloxy)-undecyl]-4-estrene-3,17-dione is stirred in 141 ml of tetrahydrofuran with 156 ml of glacial acetic acid and 78 ml of water for 2 hours at 50°. Then the mixture is concentrated to dryness under vacuum. The crude 7α-(11-hydroxyundecyl)-4-estrene-3,17-dione obtained in this way is agitated with 140 ml of pyridine and 70 ml of acetic anhydride for 15 hours at 25°. For working up the mixture, the latter is cooled to 0°, combined diluted with diethyl ether, washed with sodium bicarbonate and sodium chloride solution, dried over sodium sulfate, concentrated to dryness under vacuum, and chromatographed on silica gel with dichloromethane/ethyl acetate, yielding 22.4 g of 7α-(11-acetoxyundecyl)-4-estrene-3,17-dione, [α]D =62.4°, as an oil.

Workup

  1. concentrationThen the mixture is concentrated to dryness under vacuum
  2. customThe crude 7α-(11-hydroxyundecyl)-4-estrene-3,17-dione obtained in this way
  3. temperaturethe latter is cooled to 0°
  4. washwashed with sodium bicarbonate and sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness under vacuum
  7. customchromatographed on silica gel with dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-74326b9a8dc14b7b93b912a8a3c16230
Source dataset
uspto-grants-1992_09
Patent number
US05145847

Reaction notes

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