3,4-dihydro-2H-pyran → HCID 70466324, compound

HRID 279853Notes

Reaction equation

HRID 279853 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([CH2:12][C:13](=[O:22])[C@@H:14]2[CH2:21][C@@H:15]21)[CH2:10][CH2:9]3.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1>O1CCCC1.P(Cl)(Cl)(Cl)=O.C(OCC)C>[CH2:21]1[C@H:14]2[C:13](=[O:22])[CH2:12][C@H:11]3[C@:16]([CH3:17])([C@@H:15]12)[C@@H:18]1[C@H:8]([C@H:5]2[C@@:3]([CH2:20][CH2:19]1)([CH3:4])[C@@H:2]([O:1][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][O:23]1)[CH2:7][CH2:6]2)[CH2:9][CH2:10]3

Participants

6

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 70466008HCID 70466008, compound

Product 1

HCID 70466324HCID 70466324, compound

Reagents, catalysts & solvents 3

HCID 24813Phosphorus oxychlorideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8.0 g of 17β-hydroxy-1α,2α-methylene-5α-androstan-3-one in 40 ml of tetrahydrofuran is combined with 8 ml of 3,4-dihydro-2H-pyran and 3 drops of phosphorus oxychloride and stirred at room temperature for 30 minutes. Subsequently the mixture is diluted with diethyl ether, washed with sodium bicarbonate solution and water, dried, and evaporated, yielding 9.0 g of 1α,2α-methylene-17β-(tetrahydropyran-2-yloxy)-5α-androstan-3-one.

Workup

  1. washwashed with sodium bicarbonate solution and water
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-9c92dcb913d24bd08fc3031651a8433d
Source dataset
uspto-grants-1986_05
Patent number
US04587235

Reaction notes

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