Methanol → HCID 89650280, compound

HRID 2275988Notes

Reaction equation

HRID 2275988 reaction equation
[C:1](=[O:4])([O-])[O-:2].[Cs+].[Cs+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:15][OH:16]>C(OCC)C>[CH3:7][C:8]1[CH2:13][CH2:12][CH2:11][C:15](=[O:16])[C:9]=1[CH2:10][C:1]([O:2][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 7498Benzyl BromideHCID 10796Cesium carbonate

Product 1

HCID 89650280HCID 89650280, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of the acid (Org. Proc. Research & Dev 1997, p. 222) (2.0 g, 11.9 mmol) in MeOH (20 mL) was stirred with caesium carbonate (1.93 g, 5.94 mmol) for 1 h and the solvents were removed in vacuo. The residue was taken up in DMF (20 mL) and benzyl bromide (1.84 mL, 15.5 mmol) was added. The solution was stirred overnight at room temperature. The solution was diluted with diethylether (100 mL) and the precipitate was removed by filtration. The filtrate was washed with brine (3*50 mL), dried and concentrated. The residue was purified by flash chromatography eluting with cyclohexane and ethyl actetate (9/1 to 4/1) to give the desired compound as a colourless oil (2.8 g, 90%); 1H NMR (400 MHz, CHLOROFORM-d) 7.31-7.41 (5H, m), 5.12 (2H, s), 3.43 (2H, s), 2.42 (4H, s), 1.99 (2H, quin, J=6.2 Hz), 1.93 (3H, s).

Workup

  1. customthe solvents were removed in vacuo
  2. customthe precipitate was removed by filtration
  3. washThe filtrate was washed with brine (3*50 mL)
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with cyclohexane and ethyl actetate (9/1 to 4/1)

Sources & evidence

ORD record
ord-f48e756a59314b35b0f0799fea3b9b6c
Source dataset
uspto-grants-2015_09
Patent number
US09131688B2

Reaction notes

Loading…