3,4-dihydro-2H-pyran → HCID 20611039, compound

HRID 1838916Notes

Reaction equation

HRID 1838916 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:27])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][Br:26].[O:28]1[CH:33]=[CH:32][CH2:31][CH2:30][CH2:29]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([O:27][CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][O:28]3)=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][Br:26]

Participants

7

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 1587066311beta-Fluoro-7alpha-(5-bromopentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one

Product 1

HCID 20611039HCID 20611039, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

8.4 g of 11β-fluoro-7α-(5-bromopentyl)-3-hydroxyestra-1,3,5(10)-trien-17-one in 90 ml of tetrahydrofuran are allowed to react at room temperature with 9.0 ml of 3,4-dihydropyran and 805 mg of p-toluenesulphonic acid hydrate. After 7 h, 1 ml of triethylamine is added, and the mixture is diluted with ethyl acetate, washed with saturated sodium chloride solution until neutral and dried over sodium sulphate. Chromatography on silica gel using a hexane-ethyl acetate gradient affords 7.6 g of 11β-fluoro-7α-(5-bromopentyl)-3-(tetrahydropyran-2-yloxy)oestra-1,3,5(10)-trien-17-one as a foam.

Workup

  1. washwashed with saturated sodium chloride solution until neutral and
  2. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-0244ffd4548a480fafbcb757cd3b173c
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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