Acetic Acid → HCID 15029690, compound

HRID 1657044Notes

Reaction equation

HRID 1657044 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(OCC)=O)C.[OH:19][C:20]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:21]=1[CH:22]=O.C(O)(=O)C>O1CCCC1>[OH:19][C:20]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:21]=1/[CH:22]=[CH:11]/[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 668085-NitrosalicylaldehydeHCID 2773685tert-Butyl diethylphosphonoacetate

Product 1

HCID 15029690HCID 15029690, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Sodium hydride (content: 62%, 3.3 g) was suspended in tetrahydrofuran (30 ml). The suspension was ice-cooled in an atmosphere of argon gas. A solution of t-butyl diethylphosphonoacetate (20.9 g) in tetrahydrofuran (20 ml) was added to the suspension. The mixture was stirred for 15 min. at room temperature. A solution of 2-hydroxy-5-nitrobenzaldehyde (6.6 g) in tetrahydrofuran (20 ml) was gradually added to the mixture often with ice-cooling. The mixture was stirred for 10 min. at room temperature. Acetic acid was gradually added to the mixture until pH of the mixture was down to 5.0. The reaction mixture was gel-filtered with using YMC gel. Moreover the gel was washed with ethyl acetate. A mixture of the filtrate and washings was evaporated. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1→3:2) to give the title compound (10.0 g) having the following physical data.

Workup

  1. temperaturecooled in an atmosphere of argon gas
  2. temperaturecooling
  3. stirringThe mixture was stirred for 10 min. at room temperature
  4. filtrationThe reaction mixture was gel-filtered with using YMC gel
  5. washMoreover the gel was washed with ethyl acetate
  6. additionA mixture of the filtrate and washings
  7. customwas evaporated
  8. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1→3:2)

Sources & evidence

ORD record
ord-d60e2631686b402da36adca9e50725c3
Source dataset
uspto-grants-1993_10
Patent number
US05256686

Reaction notes

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