Water → Ergosterol, acetate

HRID 481284Notes

Reaction equation

HRID 481284 reaction equation
[CH3:1][C@@H:2]([C@@H:10]1[C@@:14]2([CH3:29])[CH2:15][CH2:16][C@@H:17]3[C@@:22]4([CH3:28])[CH2:23][CH2:24][C@H:25]([OH:27])[CH2:26][C:21]4=[CH:20][CH:19]=[C:18]3[C@@H:13]2[CH2:12][CH2:11]1)/[CH:3]=[CH:4]/[C@@H:5]([CH:7]([CH3:9])[CH3:8])[CH3:6].[C:30](OC(=O)C)(=[O:32])[CH3:31].O>N1C=CC=CC=1>[C:30]([O:27][C@H:25]1[CH2:24][CH2:23][C@@:22]2([CH3:28])[C:21](=[CH:20][CH:19]=[C:18]3[C@@H:17]2[CH2:16][CH2:15][C@@:14]2([CH3:29])[C@H:13]3[CH2:12][CH2:11][C@@H:10]2[C@H:2]([CH3:1])/[CH:3]=[CH:4]/[C@H:5]([CH3:6])[CH:7]([CH3:8])[CH3:9])[CH2:26]1)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 444679Ergosterol

Product 1

HCID 6436903Ergosterol, acetateYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 50 gm (0.13 mol) of ergosterol (1) in 300 ml of anhydrous pyridine was added 33.3 ml (0.35 mol) of acetic anhydride. The mixture was stirred at room temperature overnight and then 600 ml of water was added. The precipitate was filtered and washed three times with 200 ml portions of acetonitrile and then air dried to yield 42.0 g (74%) of (2).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed three times with 200 ml portions of acetonitrile
  3. customair dried

Sources & evidence

ORD record
ord-7b12651393e34070bd6f7c7d711280e9
Source dataset
uspto-grants-1998_08
Patent number
US05789397

Reaction notes

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