Water → HCID 54145261, compound

HRID 2255839Notes

Reaction equation

HRID 2255839 reaction equation
CO[C:3]1[CH:15]=[CH:14][C:13]([C:16]([CH3:19])(C)C)=[CH:12][C:4]=1CP(=O)(OC)OC.[H-].[Na+].[C:22]1([CH:30]=[CH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]=[CH:26][C:25](C=O)=[CH:24][CH:23]=1.O.CN([CH:42]=[O:43])C>CCOCC>[CH3:42][O:43][C:37]1[C:36]([CH:19]=[CH:16][C:13]2[CH:12]=[CH:4][CH:3]=[CH:15][CH:14]=2)=[CH:35][C:34]([C:13]([CH3:16])([CH3:14])[CH3:12])=[CH:33][C:32]=1[CH:31]=[CH:30][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 141711HCID 141711, compoundHCID 19028505HCID 19028505, compound

Product 1

HCID 54145261HCID 54145261, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of dimethyl 2-methaxy-5-tert-butylbenzylphosphonate (11) (1.01 g, 3.53 mmol) and sodium hydride (60% in oil, 0.17 g, 4.25 mmol) in dry DMF (29 ml) was cooled with stirring co 6° C. under argon. A solution of 4-stilbenecarbaldehyde (12) (0.88 g, 4.23 mmol) in dry DMF (21 ml) was added dropwise with stirring keeping the reaction temperature at 5° C. and then the reaction mixture was stirred at room temperature for 3.75 h under argon. Water (100 ml) and ether (300 ml) were added. The organic layer was separated, washed with water (3×100 ml), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography over silica (dichloromethane/hexane; 1:1) and recrystallised from dichloromethane/hexane/methanol to yield a pale yellow solid of (8) (0.95 g, 73%), m.p. 129°-129.5° C.; (Found: C, 88.06; H, 7.62. C27H28O requires C, 88.00; H, 7.66%); λmax /nm (CH2Cl2) 362 (log ε 4.72); 8H (CDCl3) 1.36 (9 H, s, tert-butyl), 3.88 (3 H, s, OCH3), 6.85 (1 H, d, JH4,H3 =8.6 Hz, H3), 7.13 (1 H, d, J=16.5 Hz, vinytic H), 7.125 (1 H, s, vinytic H), 7.26 H, m, H4"), 7.28 (1 H, dd, JH4 =8.6 Hz, JH6,H4 =2.44 Hz, H4), 7.37 (2 H, m, H3" and H5"), 7.53 (7 H, m, H2", H6", H2', H3', H5', H6', and vinylic H), 7.56 (2 H, m, H2' and H6') and 7.62 (1 H, d, JH4,H3 =2.4 Hz, H6); δC (CDCl3) 31.5 (CH3), 34.1 [C(CH3)3 ], 55.6 (OCH3), 110.5, 123.5,124.0, 125.6, 126.5, 126.7, 126.8, 127.5, 128.2, 128.4, 128.7, 136.3, 137.4, 137.5, 143.3 and 154.8; m/z 368.214.

Workup

  1. temperaturewas cooled
  2. customco 6° C. under argon
  3. stirringwith stirring
  4. customat 5° C.
  5. stirringthe reaction mixture was stirred at room temperature for 3.75 h under argon
  6. customThe organic layer was separated
  7. washwashed with water (3×100 ml)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by column chromatography over silica (dichloromethane/hexane; 1:1)
  12. customrecrystallised from dichloromethane/hexane/methanol

Sources & evidence

ORD record
ord-0901c59951d440468cbb8e9bfca9d923
Source dataset
uspto-grants-1997_08
Patent number
US05653914

Reaction notes

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