Acetic Anhydride → HCID 9929412, compound

HRID 2108334Notes

Reaction equation

HRID 2108334 reaction equation
[CH2:1]1[CH2:24][O:23][C:3]2([CH2:8][CH2:7][C@H:6]3[C@H:9]4[C@H:19]([CH2:20][CH2:21][C@:4]23[CH3:5])[C@:17]2([CH3:18])[C:12]([CH2:13][C@@H:14]([OH:22])[CH:15]=[CH:16]2)=[CH:11][CH2:10]4)[O:2]1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1>[C:25]([O:22][C@H:14]1[CH:15]=[CH:16][C@@:17]2([CH3:18])[C:12](=[CH:11][CH2:10][C@@H:9]3[C@@H:19]2[CH2:20][CH2:21][C@@:4]2([CH3:5])[C@H:6]3[CH2:7][CH2:8][C:3]32[O:2][CH2:1][CH2:24][O:23]3)[CH2:13]1)(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 57629370HCID 57629370, compound

Product 1

HCID 9929412HCID 9929412, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of crude 17,17-ethylenedioxyandrosta-1.5-dien-3β-ol (4, 1.2 g) in pyridine (10 ml) and acetic anhydride (3 ml) was stirred at room temperature for 16 hours. The reaction mixture was poured into ice-water and the compound was extracted with ether. The organic layer was washed with ice-water several times followed by brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent in vacuo below 35° C. gave 1.0 g of crude solid. Recrystallization from methanol gave 3β-acetoxy-17,17-ethylenedioxyandrosta-1,5-diene (5). Mp. 105-6° C.

Workup

  1. extractionthe compound was extracted with ether
  2. washThe organic layer was washed with ice-water several times
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent in vacuo below 35° C.
  5. customgave 1.0 g of crude solid
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-c35149602ede4a0ca33686c35f7191ca
Source dataset
uspto-grants-2009_04
Patent number
US07514420B2

Reaction notes

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