Sulfuric Acid → HCID 56635183, compound

HRID 543642Notes

Reaction equation

HRID 543642 reaction equation
S(=O)(=O)(O)O.[OH:6][C@H:7]1[CH2:24][C@@:23]2([CH3:25])[C@@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]3[CH2:15][CH2:16][C:17]2=[O:26])[CH2:9][CH2:8]1>C(OC(C)=C)(=O)C>[C:7]([O:6][C@H:7]1[CH2:24][C@@:23]2([CH3:25])[C@@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]3[CH2:15][CH:16]=[C:17]2[O:26][C:17](=[O:26])[CH3:16])[CH2:9][CH2:8]1)(=[O:6])[CH3:8]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 18644453HCID 18644453, compound

Product 1

HCID 56635183HCID 56635183, compoundYield 137.2%

Reagents, catalysts & solvents 1

HCID 7916Isopropenyl acetateSolvent2×

Procedure

A portion (17.23 ml) of a solution of concentrated sulphuric acid (0.4 ml) in isopropenyl acetate (20 ml) was added dropwise to a solution of 2β-hydroxy-5α-androstan-17-one (27.57 g) in isopropenyl acetate (140 ml). The solvent was removed slowly by distillation through a Vigreux column at such a rate that the solution was concentrated to approx. 60 ml after 6 h. The reaction mixture was cooled in an ice-bath to give a crystalline product, which was filtered off and washed with hexane (300 ml). The crop (33.21 g) in toluene was filtered through a column of silica gel (660 g; 0.2-0.5 mm); the eluate was evaporated to dryness and the residue was crystallised from acetone to afford 5α-androst-16-ene-2β,17-diol diacetate (24.38 g), m.p. 133°-134° C.; [α]D +34.4° (c 0.61 in CHCl3).

Workup

  1. customThe solvent was removed slowly by distillation through a Vigreux column at such a rate that the solution
  2. concentrationwas concentrated to approx. 60 ml after 6 h
  3. temperatureThe reaction mixture was cooled in an ice-bath
  4. customto give a crystalline product, which
  5. filtrationwas filtered off
  6. washwashed with hexane (300 ml)
  7. filtrationThe crop (33.21 g) in toluene was filtered through a column of silica gel (660 g; 0.2-0.5 mm)
  8. customthe eluate was evaporated to dryness
  9. customthe residue was crystallised from acetone

Sources & evidence

ORD record
ord-dc9c80a30c504a328c7dfb9efa240bca
Source dataset
uspto-grants-1984_05
Patent number
US04447425

Reaction notes

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