Water → HCID 67976021, compound

HRID 508618Notes

Reaction equation

HRID 508618 reaction equation
[CH:1]([C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[N:4]=1)=O.[H-].[Na+].[OH2:27].[CH2:28]1[CH2:32][O:31][CH2:30][CH2:29]1>>[CH2:32]([O:31][C:30](=[O:27])/[CH:29]=[CH:1]/[C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]([C:15]2[CH:20]=[CH:19][C:18]([S:21](=[O:22])(=[O:23])[NH2:24])=[CH:17][CH:16]=2)[N:4]=1)[CH3:28]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86045712HCID 86045712, compound

Product 1

HCID 67976021HCID 67976021, compoundYield 73%

Procedure

To a solution of aldehyde 12c (0.16 g, 0.47 mmol) and triethyl phosphonoacetate (0.12 g, 0.52 mmol) in 5 mL of THF was added 60% sodium hydride in oil (21 mg, 0.52 mmol) at 0° C. The reaction mixture was stirred for 1 hour. After adding 5 mL of water, the mixture was extracted with EtOAc. After drying with MgSO4, the solvent was removed in vacuo. The resulting white solid was filtered and washed with hexanes to give the titled compound (0.14 g, 73% yield) as a white solid. mp 166.8-171.2° C. 1H NMR (300 MHz, CDCl3): δ 7.88 (d, J=9 Hz, 2H), 7.72 (d, J=16 Hz, 1H), 7.45 (d, J=9 Hz, 2H), 7.20-7.08 (m, 4H), 6.70 (s, 1H), 6.52 (d, J=16 Hz, 1H), 4.90 (s, 2H), 4.27 (q, J=7 Hz, 2H), 2.38 (s, 3H), 1.34 (t, J=7 Hz, 3H).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialAfter drying with MgSO4
  3. customthe solvent was removed in vacuo
  4. filtrationThe resulting white solid was filtered
  5. washwashed with hexanes

Sources & evidence

ORD record
ord-f822e9bbd1754968898da34da94c6bc7
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

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