Formaldehyde → 2-(6-Bromo-pyridin-2-yl)-3-hydroxy-2-hydroxymethyl-propionic acid ethyl ester

HRID 538301Notes

Reaction equation

HRID 538301 reaction equation
C=O.[O-:3][CH2:4]C.[Na+].[CH2:7]([O:9][C:10](=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[N:13]=1)[CH3:8].[C:20](OCC)(=[O:22])C>C1COCC1.CCCCCC>[CH2:7]([O:9][C:10](=[O:19])[C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[N:13]=1)([CH2:4][OH:3])[CH2:20][OH:22])[CH3:8]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 2723922Sodium ethoxideHCID 53419420Ethyl 2-(6-bromopyridin-2-yl)acetate

Product 1

HCID 866680162-(6-Bromo-pyridin-2-yl)-3-hydroxy-2-hydroxymethyl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To the solution of para formaldehyde (9.6 g, 319.55 mmol) and sodium ethoxide (0.87 g, 12.784 mmol) in dry THF (250 ml) was added (6-bromo-pyridin-2-yl)-acetic acid ethyl ester (31.2 g, 127.82 mmol) at 0° C. to −10° C. and allowed the reaction mixture to stir at same temperature for 4 h. Solids formed in the reaction mixture were filtered and washed with ethyl acetate and the filtrate was concentrated to obtain crude product as a brown liquid. Yield=30.0 g (crude). TLC (30% ethyl acetate in hexane) Rf=0.28; LCMS: RtH8=0.702, M+1=304.0 and 306.0.

Workup

  1. customSolids formed in the reaction mixture
  2. filtrationwere filtered
  3. washwashed with ethyl acetate
  4. concentrationthe filtrate was concentrated
  5. customto obtain crude product as a brown liquid

Sources & evidence

ORD record
ord-b879ffd16b1c4ccd9bfaf5c4cbc54d90
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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