16alpha-Hydroxyestrone → HCID 22837741, compound

HRID 649127Notes

Reaction equation

HRID 649127 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[C@H:10]([OH:21])[CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1>N1C=CC=CC=1.C(OC(=O)CCC)(=O)CCC.CN(C)C1C=CN=CC=1.C(OCC)C>[C:2]([O:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[C@H:10]([O:21][C:11](=[O:20])[CH2:10][CH2:9][CH3:8])[CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1)(=[O:1])[CH2:3][CH2:4][CH3:17]

Participants

6

Reactant 1

HCID 11511616alpha-Hydroxyestrone

Product 1

HCID 22837741HCID 22837741, compoundYield 80.6%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 7798Butyric anhydrideSolvent

Procedure

A solution of 2.0 g of 3,16α-dihydroxy-1,3,5(10)-estratrien-17-one in 10 ml of pyridine and 5 ml of butyric anhydride is allowed to stand at room temperature for 15 hours with the addition of 100 mg of 4-dimethylaminopyridine. The reaction mixture is diluted with diethyl ether, washed with water, dried over sodium sulfate, and evaporated. The residue is chromatographed on silica gel with a pentane-diethyl ether gradient (0-30% diethyl ether), yielding 1.2 g of 3,16α-dibutyryloxy-1,3,5(10)-estratrien-17-one as an oil.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe residue is chromatographed on silica gel with a pentane-diethyl ether gradient (0-30% diethyl ether)

Sources & evidence

ORD record
ord-027f42199d994f3da6a10723bc7f7c52
Source dataset
uspto-grants-1988_04
Patent number
US04738957

Reaction notes

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