Dimethoxymethane → HCID 67608852, compound

HRID 1847107Notes

Reaction equation

HRID 1847107 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].[CH3:30][O:31][CH2:32]OC.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[CH3:30][O:31][CH2:32][O:27][CH: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

Participants

4

Reactant 3

HCID 8020DimethoxymethaneHCID 14812Phosphorus oxide (P4O10)HCID 444679Ergosterol

Product 1

HCID 67608852HCID 67608852, compoundYield 89%

Procedure

Ergosterol (35.7 g, 90.0 mmol) was dissolved in dimethoxymethane (350 mL, 6.3 mol), and diphosphorous pentoxide (17.9 g, 126 mmol) was added thereto, followed by stirring at room temperature for 1 hour. Diatomaceous earth was added to the reaction mixture, followed by stirring for 30 minutes and filtration, and the filtrate was concentrated. Ethyl acetate was added to the resulting residue for trituration to obtain the title compound (35.1 g, 89%).

Workup

  1. additionDiatomaceous earth was added to the reaction mixture
  2. stirringby stirring for 30 minutes
  3. filtrationfiltration
  4. concentrationthe filtrate was concentrated
  5. additionEthyl acetate was added to the resulting residue for trituration

Sources & evidence

ORD record
ord-6f4b20f1f4554a2a9a994bbcba8ece88
Source dataset
uspto-grants-2015_02
Patent number
US08952003B2

Reaction notes

Loading…