Sodium hydride → HCID 69927397, compound

HRID 2416406Notes

Reaction equation

HRID 2416406 reaction equation
[H-].[Na+].C(O[C:12]1[CH:19]=[C:18]([CH:20]=[CH:21][C:22]2[CH:27]=[CH:26][C:25]([CH:28]=[CH2:29])=[CH:24][CH:23]=2)[C:17]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:16][C:13]=1[CH:14]=O)CCCCCCC.[Br-].[CH2:40]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[CH2:31]([O:30][C:17]1[C:16]([O:30][CH2:17][CH2:16][CH2:13][CH2:12][CH2:19][CH2:18][CH2:20][CH3:21])=[C:13]([CH:14]=[CH:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:12]=[CH:19][C:18]=1[CH:20]=[CH:21][C:22]1[CH:23]=[CH:24][C:25]([CH:28]=[CH2:29])=[CH:26][CH:27]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 2734970Benzyltriphenylphosphonium bromideHCID 85432955HCID 85432955, compound

Product 1

HCID 69927397HCID 69927397, compound

Procedure

Solid NaH (300 mg, 12.4 mmol) was added in small portions into a suspension of 2,5-dioctoxy-4-(4′-vinylstyryl)benzaldehyde (1.27 g, 2.59 mmol) and benzyltriphenylphosphonium bromide (1.35 g, 3.11 mmol). The reaction mixture was stirred under nitrogen at room temperature for 24 hours. The reaction was quenched slowly with water, extracted with CH2Cl2, washed with brine, dried over MgSO4 and the solvent was evaporated under reduced pressure. The crude product was purified on a silica gel column (25-40% CHCl3/hexanes) to give a greasy yellow solid which is a mixture of cis and trans isomers. Yield 1.2 g (82%). 1H NMR (CDCl3): δ 7.51 (d, J=9.26 Hz, 2H), 7.47 (d, J=9.25 Hz, 1H), 7.42 (s, 2H), 7.29 (d, J=7.36 Hz, 2H), 7.25 (dd, J1=6.38 Hz, J2=7.36 Hz, 2H), 7.18 (t, J=7.34 Hz, 1H), 7.14 (s, 1H), 6.76 (d, J=11.97 Hz, 1H), 6.72 (dd, J1=17.72 Hz, J2=10.85 Hz, 1H), 6.34 (d, J=12.00 Hz, 1H), 5.78 (d, J=17.72 Hz, 1H), 5.25 (d, J=10.85 Hz, 1H), 4.02 (t, J=6.54 Hz, 2H), 3.55 (t, J=6.87 Hz, 2H), 1.78 (m, 4H), 1.64 (m, 4 H), 1.23-1.42 (m, 16H), 0.90 (m, 6H). 13C NMR (CDCl3): δ 151.34, 150.35, 137.89, 137.79, 136.81, 136.72, 130.24, 129.12, 128.49, 128.36, 127.14, 126.84, 126.73, 126.70, 125.62, 123.74, 114.81, 113.71, 110.37, 69.56, 69.16, 32.06, 29.61, 29.51, 26.33, 22.90, 14.35. FABMS: m/z 564 (M+).

Workup

  1. customThe reaction was quenched slowly with water
  2. extractionextracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customthe solvent was evaporated under reduced pressure
  6. customThe crude product was purified on a silica gel column (25-40% CHCl3/hexanes)
  7. customto give a greasy yellow solid which
  8. additiona mixture of cis and trans isomers

Sources & evidence

ORD record
ord-13ca65754e8c4fa88931b70e804daa39
Source dataset
uspto-grants-2004_11
Patent number
US06824890B2

Reaction notes

Loading…