Acetic Anhydride → HCID 86733694, compound

HRID 918055Notes

Reaction equation

HRID 918055 reaction equation
[OH:1][C@@H:2]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:20]2[C:19](=[O:25])[CH2:18][C@@:17]2([CH3:26])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:16])[CH2:13][O:14][CH3:15])[CH2:3]1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>N1C=CC=CC=1>[C:27]([O:1][C@@H:2]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:20]2[C:19](=[O:25])[CH2:18][C@@:17]2([CH3:26])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:16])[CH2:13][O:14][CH3:15])[CH2:3]1)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86733695HCID 86733695, compound

Product 1

HCID 86733694HCID 86733694, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3α-hydroxy-21-methoxy-5α-pregnane-11,20-dione (0.2 g.) in pyridine (1.0 ml.) was treated with acetic anhydride (0.2 ml.) at room temperature for 16 hours. The mixture was then partitioned between ether and 2N-hydrochloric acid and the organic layer was washed with water, dried (Na2SO4) and evaporated. The residue was recrystallised from acetone/petroleum ether to give 3α-acetoxy-21-methoxy-5α-pregnane-11,20-dione (0.17 g.) as white needles; m.p. 93°; [α]D + 107°, (c 0.7).

Workup

  1. customThe mixture was then partitioned between ether and 2N-hydrochloric acid
  2. washthe organic layer was washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was recrystallised from acetone/petroleum ether

Sources & evidence

ORD record
ord-fbfa7b8d42984059a242630ec4ae9026
Source dataset
uspto-grants-1976_07
Patent number
US03969345

Reaction notes

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