Diethyl Ether → HCID 54033643, compound

HRID 2255841Notes

Reaction equation

HRID 2255841 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:4]=1[CH2:5]P(=O)(OC)OC.[H-].[Na+].[OH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1.CCOCC>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:4]=1[CH:5]=[CH:32][C:31]1[CH:30]=[CH:29][C:28]([O:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][OH:20])=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 150510824-(6-Hydroxyhexoxy)benzaldehydeHCID 19028488HCID 19028488, compound

Product 1

HCID 54033643HCID 54033643, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
6 °C

Procedure

A mixture of dimethyl 2,5-dimethoxybenzylphosphonate (2.92 g, 11.2 mmol) and sodium hydride (60% in oil, 1.08 g, 27.0 mmol) in dry DMF (92 ml) was cooled with in an ice-bath under argon. To this was added dropwise a solution of 4-(6-hydroxyhexyloxy)benzaldehyde (13) (2.50 g, 11.3 mmol) in dry DMF (55 ml). The reaction mixture was stirred at 6° C. for 1.5 h and then at room temperature for 4 h. Ether (300 ml) and water (250 ml) were added and the mixture shaken well. The organic layer was separated and washed with water (4×250 ml), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography over silica (dichloromethane/methanol; 19:1 yield (14) (1.89 g, 47%) as an oil; δH (CDCl3) 1.46 (4 H, m, CH2), 1.60 (2 H, m, CH2), 1.79 (2 H, m, CH2), 3.65 (2 H, t, J =6.6 Hz, OCH2), 3.81 (3 H, s, OCH3), 3.83 (3 H, s OCH3), 3.96 (2 H, t, J=6.5 Hz, OCH2), 6.76 (1 H, dd, JH3', JH4 '=8.9 Hz, JH6',H4' =3.0 Hz, H4'), 6.82 (1 H, d, JH4',H3' =8.9 Hz, H3'), 6.87 and 7.45 (4 H, AA'BB', PhH), 7.03 (1 H, d, J=16.5 Hz, vinylic H), 7.13 (1 H, d, JH4',H6' =3.0 HZ, H6') and 7.31 H, d, J=16.5 Hz, vinylic H); δc (CDCl3) 25.5, 25.6, 29.2, 32.6, 55.7, 56.2, 62.8, 67.8, 111.3, 112.2, 113.1, 114.5, 120.7, 127.6, 127.7, 128.7, 130.4, 151.2, 153.7 and 158.7.

Workup

  1. temperaturewas cooled with in an ice-bath under argon
  2. waitat room temperature for 4 h
  3. stirringthe mixture shaken well
  4. customThe organic layer was separated
  5. washwashed with water (4×250 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography over silica (dichloromethane/methanol; 19:1 yield (14) (1.89 g, 47%) as an oil; δH (CDCl3) 1.46 (4 H, m, CH2), 1.60 (2 H, m, CH2), 1.79 (2 H, m, CH2), 3.65 (2 H, t, J =6.6 Hz, OCH2), 3.81 (3 H, s, OCH3), 3.83 (3 H, s OCH3), 3.96 (2 H, t, J=6.5 Hz, OCH2), 6.76 (1 H, dd, JH3', JH4 '=8.9 Hz, JH6',H4' =3.0 Hz, H4'), 6.82 (1 H, d, JH4',H3' =8.9 Hz, H3'), 6.87 and 7.45 (4 H, AA'BB', PhH), 7.03 (1 H, d, J=16.5 Hz, vinylic H), 7.13 (1 H, d, JH4',H6' =3.0 HZ, H6') and 7.31 H, d, J=16.5 Hz, vinylic H)

Sources & evidence

ORD record
ord-4a4822eec79a44f68c828bf137cc03d8
Source dataset
uspto-grants-1997_08
Patent number
US05653914

Reaction notes

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