Tris(hydroxymethyl)aminomethane → (Chroman-5-yloxy)-acetic acid methyl ester

HRID 2307874Notes

Reaction equation

HRID 2307874 reaction equation
[O:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([OH:11])[C:5]=2[CH2:4][CH2:3][CH2:2]1.Br[CH2:13][C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+].C(O)C(N)(CO)CO>C(#N)C>[CH3:17][O:16][C:14](=[O:15])[CH2:13][O:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][CH2:2][O:1]2

Participants

6

Reactant 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 113670873,4-Dihydro-2H-1-benzopyran-5-ol

Product 1

HCID 11322001(Chroman-5-yloxy)-acetic acid methyl esterYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of chroman-5-ol (2.1 g, 14 mmol), methyl bromoacetate (1.6 mL, 16.8 mmol), and cesium carbonate (6.8 g, 21 mmol) in 50 mL acetonitrile was heated at 60° C. for 3 hours. PS-Trisamine scavenger resin was then added to the warmed solution followed by an additional 30 minutes heating. The reaction mixture was then cooled and filtered. The filtrate was collected, diluted with 100 mL ether, washed with brine (1×50 mL), dried (Na2SO4), and the solvent removed in vacuo to give 2.1 g (68%) of the title compound, pure enough for subsequent use. 400 MHz 1H NMR (DMSO-d6) δ 6.92 (t, 1H, J=8.3 Hz), 6.33 (d, 1H, J=8.3 Hz), 6.31 (d, 1H, J=8.3 Hz), 4.72 (s, 2H), 4.02 (t, 2H, J=5.1 Hz), 3.64 (s, 3H), 2.56 (t, 2H, J=6.6 Hz), 1.83 (m, 2H).

Workup

  1. temperatureheating
  2. temperatureThe reaction mixture was then cooled
  3. filtrationfiltered
  4. customThe filtrate was collected
  5. additiondiluted with 100 mL ether
  6. washwashed with brine (1×50 mL)
  7. dry with materialdried (Na2SO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-59f17f1f8fd945d485528760917146e2
Source dataset
uspto-grants-2004_12
Patent number
US06833380B2

Reaction notes

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