Formaldehyde → HCID 86724287, compound

HRID 594886Notes

Reaction equation

HRID 594886 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=[O:12].[CH2:13]=[O:14].N1CCC[C@H]1[C:17]([OH:19])=O.[OH-].[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][C:6]([CH2:17][OH:19])([CH2:13][OH:14])[C:5]2=[O:12]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 41974516-bromo-3,4-dihydro-2H-1-benzopyran-4-one

Product 1

HCID 86724287HCID 86724287, compoundYield 216.9%

Procedure

A mixture of 6-bromo-2,3-dihydro-4H-chromen-4-one (0.3 g, 1.3 mmol), paraformaldehyde (0.48 g), L-proline (61 mg, 0.53 mmol), and 0.2 M aqueous sodium hydroxide (6 mL) was stirred at room temperature for 16 hours. The mixture was extracted with CHCl3 and concentrated in vacuo. The residue was purified with silica-gel column chromatography (CHCl3/MeOH=100:0 to 90:10) to give 6-bromo-3,3-bis(hydroxymethyl)-2,3-dihydro-4H-chromen-4-one (0.33 g).

Workup

  1. extractionThe mixture was extracted with CHCl3
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified with silica-gel column chromatography (CHCl3/MeOH=100:0 to 90:10)

Sources & evidence

ORD record
ord-c51a4467a0b4458fb53b994ddb864a27
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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