Formaldehyde → 5,10-Methylene-THF

HRID 1463264Notes

Reaction equation

HRID 1463264 reaction equation
[C:1]1(S(O)(=O)=O)C=CC=CC=1.[C:11]([OH:42])(=[O:41])[CH2:12][CH2:13][C@H:14]([NH:18][C:19]([C:21]1[CH:40]=[CH:39][C:24]([NH:25][CH2:26][C@@H:27]2[NH:38][C:37]3[C:35](=[O:36])[NH:34][C:32]([NH2:33])=[N:31][C:30]=3[NH:29][CH2:28]2)=[CH:23][CH:22]=1)=[O:20])[C:15]([OH:17])=[O:16].[OH-].[Na+].C=O.S(=O)(=O)(O)O>O>[CH2:1]1[N:25]([C:24]2[CH:23]=[CH:22][C:21]([C:19](=[O:20])[NH:18][C@H:14]([C:15]([OH:17])=[O:16])[CH2:13][CH2:12][C:11]([OH:42])=[O:41])=[CH:40][CH:39]=2)[CH2:26][C@@H:27]2[N:38]1[C:37]1[C:35](=[O:36])[NH:34][C:32]([NH2:33])=[N:31][C:30]=1[NH:29][CH2:28]2

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 137226505HCID 137226505, compound

Product 1

HCID 1353986455,10-Methylene-THF

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 g of pure (6S)-tetrahydrofolic acid benzenesulfonate prepared, for example, by the method described in Swiss Patent Application No. 108, filed January 16, 1991, are suspended in water. The pH is brought to 7.5 by addition of I N sodium hydroxide solution. 15 ml of 37% strength aqueous formaldehyde solution are then added, and the mixture is adjusted to pH 2.5 with 2 N sulfuric acid. The 5,10-methylene-(6R)-tetrahydrofolic acid formed precipitates and is filtered off.

Sources & evidence

ORD record
ord-8cc10633833840e8bcb8178cc8aecc36
Source dataset
uspto-grants-1994_04
Patent number
US05300505

Reaction notes

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