Glyoxylic Acid → 58207-08-2

HRID 1977491Notes

Reaction equation

HRID 1977491 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=O.C([N:15](CC1C=CC(OC)=CC=1)C)C1C=CC(OC)=CC=1.[C:26]1([CH:32]=[CH:33]B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[NH2:15][CH:2](/[CH:33]=[CH:32]/[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:1]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 760Glyoxylic AcidHCID 27343812-Phenylvinylboronic acidHCID 19866082HCID 19866082, compound

Product 1

HCID 588530958207-08-2Yield 202.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of glyoxylic acid (110 mg, 1.2 mmol) in toluene (12 mL) was added di-(p-anisyl)-methylamine (291 mg, 1.2 mmol) in one portion. After 1 min, 2-phenylethenyl boronic acid (177 mg, 1.2 mmol) was added and the reaction mixture was stirred vigorously for 12 hours. The precipitated product was isolated by filtration, washed with dichloromethane (15 mL), toluene (10 mL) and dried under vacuum to give the expected product (430 mg, 89% yield). 1H-NMR (360 MHz, CD3OH) d 6.8-7.5 (m, 13H), 6.60 (d, J=15.5 Hz, 1H), 6.25 (dd, J=15.5 Hz, 9.5 Hz, 1H), 5.49 (s, 1H), 4.00 (d, J=9.5 Hz, 1H), 3.75 (s, 6H), 2.3 (s, 1H).

Workup

  1. customThe precipitated product was isolated by filtration
  2. washwashed with dichloromethane (15 mL), toluene (10 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-0bfb312c17aa449aa1541e20b4aa9604
Source dataset
uspto-grants-2001_05
Patent number
US06232467B1

Reaction notes

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