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

HRID 1461987Notes

Reaction equation

HRID 1461987 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-00f58e660fe644d7a111bc9770c97b2a
Source dataset
uspto-grants-1984_07
Patent number
US04457925

Reaction notes

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