Methanol → Diisopropyl Ether

HRID 1649472Notes

Reaction equation

HRID 1649472 reaction equation
C([Si](CC1C=CC=CC=1)(CC1C=CC=CC=1)[O:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@:12]3([O:32][C@@H:13]3[C@@H:14]([Cl:31])[C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[C@@H:17]3[CH2:30][C@@H:18]3[C:19]2=[O:29])[CH2:11]1)C1C=CC=CC=1.[CH3:47]O.S(=O)(=O)(O)O>O1CCCC1.CCOCC>[CH:13]([O:32][CH:12]([CH3:11])[CH3:25])([CH3:14])[CH3:47].[Cl:31][C@@H:14]1[C@H:13]2[O:32][C@:12]32[C@:25]([CH3:28])([CH2:26][CH2:27][C@H:10]([OH:9])[CH2:11]3)[C@@H:24]2[C@@H:15]1[C@H:16]1[C@@:20]([CH2:22][CH2:23]2)([CH3:21])[C:19](=[O:29])[C@H:18]2[CH2:30][C@@H:17]12

Participants

7

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 886873723beta-Tribenzylsilyloxy-7alpha-chloro-5,6beta-epoxy-15beta,16beta-methylene-5beta-androstan-17-one

Product 2

HCID 7914Diisopropyl EtherHCID 130759667alpha-Chloro-5,6beta-epoxy-3beta-hydroxy-15beta,16beta-methylene-5beta-androstan-17-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

19 g of 3β-tribenzylsilyloxy-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one is dissolved in 50 ml of tetrahydrofuran and 50 ml of methanol and agitated with 15 ml of 8% sulfuric acid for 2 hours at room temperature. The mixture is thereafter diluted with ether, washed with saturated sodium bicarbonate solution and water, dried over sodium sulfate, and concentrated under vacuum. By trituration of the thus-obtained solid with diisopropyl ether, 8.7 g of 7α-chloro-5,6β-epoxy-3β-hydroxy-15β,16β-methylene-5β-androstan-17-one is obtained, mp 172° C.

Workup

  1. washwashed with saturated sodium bicarbonate solution and water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-43742ca05f444fbea7f166e062d76328
Source dataset
uspto-grants-1983_11
Patent number
US04416985

Reaction notes

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