Cesium carbonate → HCID 85850168, compound

HRID 898203Notes

Reaction equation

HRID 898203 reaction equation
[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=2[OH:13])[CH:8]=[O:9])[CH2:3][CH2:2]1.I[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=2[O:13][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:8]=[O:9])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 202751-IodononaneHCID 114010943-CYCLOPROPOXY-4-HYDROXY-BENZALDEHYDE

Product 1

HCID 85850168HCID 85850168, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.78 g (10.0 mmol) of 3-(cyclopropyloxy)-4-hydroxybenzaldehyde and 2.54 g (10.0 mmol) of 1-iodononane in 20 mL acetonitrile was added 3.58 g (11.0 mmol) of Cs2CO3. The slurry was stirred at rt for 12 h. The reaction was quenched with 30 mL of water and extracted with ethyl acetate (50 mL×2). The combined extractions were washed with water, dried with sodium sulfate and concentrated to a solid. Flash chromatography on a Biotage 40M cartridge using 10% ethyl acetate/hexanes afforded 2.9 g (95%) of the title compound as a white solid. 1H NMR (500 Mhz) δ 0.87-0.91 (m, 7H), 1.30-1.90 (m, 14H), 3.85 (m, 1H), 4.10 (t, J=6.9, 2H), 6.98 (d, J=8.2, 1H), 7.48 (dd, J=8.5, 1.8, 1H), 7.77 (d, J=1.8, 1H), 9.89 (s, 1H); LC-1: 4.6 min; ESI-MS 305 (M+H).

Workup

  1. customThe reaction was quenched with 30 mL of water
  2. extractionextracted with ethyl acetate (50 mL×2)
  3. extractionThe combined extractions
  4. washwere washed with water
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated to a solid

Sources & evidence

ORD record
ord-25aa40f4e3c84429b498fdae1c9dbcce
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

Loading…