Water → Ergosterol, acetate

HRID 1068557Notes

Reaction equation

HRID 1068557 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-2d634b5c77b64708b1ae0f4ac4a06bb6
Source dataset
uspto-grants-2001_06
Patent number
US06251883B1

Reaction notes

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