Sodium Methoxide → HCID 131722941, compound

HRID 413561Notes

Reaction equation

HRID 413561 reaction equation
C([O:4][CH2:5][C@@:6]1([CH2:20][O:19][C@H:18]([CH2:21][O:22]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@@H:8]1[O:9]C(=O)C)[OH:7])(=O)C.C[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:20]1[O:19][C@H:18]([CH2:21][OH:22])[C@@H:13]([OH:14])[C@H:8]([OH:9])[C@:6]1([OH:7])[CH2:5][OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 131722942HCID 131722942, compound

Product 1

HCID 131722941HCID 131722941, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

1,3,4,6-Tetra-O-acetyl-2,5-O-methylene-D-mannitol 17 (2.8 kg, 7.73 mol) was added to chloroform (14 lit.) in 25 lit. round bottom flask with mechanical stirring. The reaction mixture was cooled to 0° C., and 0.5% NaOMe solution (6.5 lit.) was added slowly. The reaction mixture was stirred for 3 hours. The solid was filtered and dried to provide 1.0 kg (67%) of 2,5-O-methylene-D-mannitol 18, m.p. 172-173° C., [α]D−52° (c 1.18, CHCl3), TLC (silica gel), 1:4, methanol: chloroform, Rf=0.8. 1H NMR (D2O): δ 3.42 (m, 2H), 3.72 (m, 4H), 3.97 (m, 2H), 4.91 (s, 2H).

Workup

  1. filtrationThe solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-97b4403d9112471ab1d6b91ec57d364a
Source dataset
uspto-grants-2003_05
Patent number
US06566538B1

Reaction notes

Loading…