HCID 86713710, compound → HCID 86713711, compound

HRID 1406039Notes

Reaction equation

HRID 1406039 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][C:10](=[CH:14][O:15]C)[CH2:9]2)=[CH:4][CH:3]=1>C(O)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH:10]([CH:14]=[O:15])[CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86713710HCID 86713710, compound

Product 1

HCID 86713711HCID 86713711, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

Crude C5 (1.25 g from the preceding step, ≦4.8 mmol) was dissolved in aqueous formic acid (3 M, 2.0 mL) and the mixture was refluxed for 2 hours. The solution was cooled to room temperature, diluted with water and extracted twice with ethyl acetate; the combined organic layers were dried over sodium sulfate and concentrated in vacuo. Silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptanes) afforded the title compound as an oil, presumed by 1H NMR to be a roughly 4:1 mixture of the two stereoisomers. Yield: 338 mg, 1.52 mmol, 32% over two steps. GCMS m/z 222 (M+). 1H NMR (400 MHz, CDCl3) δ [9.65 (d, J=1.4 Hz) and 9.79 (br s), total 1H], 7.25-7.30 (m, 2H), 7.12-7.18 (m, 2H), 1.21-2.66 (m, 10H).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. extractionextracted twice with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39e457a925c641a2bdc5ed02c0840c28
Source dataset
uspto-grants-2014_12
Patent number
US08916564B2

Reaction notes

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