Sulfuric Acid → HCID 70466764, compound

HRID 279856Notes

Reaction equation

HRID 279856 reaction equation
[C:1]([O:4][CH:5]1[C@@H:22]2[CH2:23][C@@H:21]2[C@@:20]2([CH3:24])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:25]C2CCCCO2)[CH2:6]1)(=[O:3])[CH3:2].S(=O)(=O)(O)O>O1CCCC1.CO.C(OCC)C>[C:1]([O:4][CH:5]1[C@@H:22]2[CH2:23][C@@H:21]2[C@@:20]2([CH3:24])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[OH:25])[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 70466750HCID 70466750, compound

Product 1

HCID 70466764HCID 70466764, compoundYield 79.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11 g of 3-acetoxy-1α,2α-methylene-17β-(tetrahydropyran-2-yloxy)-5α-androstane in 55 ml of tetrahydrofuran and 55 ml of methanol is combined with 11 ml of 8% strength sulfuric acid and stirred for 3 hours at room temperature. The reaction solution is diluted with diethyl ether, washed with water, dried, and evaporated. The residue is chromatographed on silica gel, yielding 7.0 g of 3-acetoxy-1α,2α-methylene-5α-androstan-17β-ol.

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated
  4. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-69a8f25fa6f447ad93ba20c2471a3b1f
Source dataset
uspto-grants-1986_05
Patent number
US04587235

Reaction notes

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