HCID 14317723, compound → HCID 66636992, compound

HRID 2425569Notes

Reaction equation

HRID 2425569 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].C(C1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=[CH:13]2)(=O)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:1]=[C:2]([C:5]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=[CH:13]2)[CH3:3]

Participants

5

Reactant 2

HCID 14317723HCID 14317723, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 66636992HCID 66636992, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

A suspension of methyl triphenylphosphonium bromide (2.41 g, 6.74 mmol) in THF (20 ml) was added dropwise potassium tert-butoxide (756 mg, 6.74 mmol) in THF (20 ml) at 0° C., and the mixture was stirred at room temperature for 1.5 hours. Then, methyl 6-acetyl-2-naphthoate (J. Org. Chem., 1990, 55, 319-324, 769 mg, 3.37 mmol) in THF (5 ml) was added at room temperature, and the resulting mixture was stirred at room temperature for 2 hours. The reaction was quenched with water (100 ml) and extracted with ethyl acetate-hexane (1:2). The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude material was purified by silica gel column chromatography, eluting with ethyl acetate-hexane (0:100 to 1:20) to give 0.67 g (88% yield) of the title compound as white solid. 1H NMR (270 MHz, CDCl3) δ 2.28 (3H, s), 3.99 (3H, s), 5.26 (1H, s), 5.58 (1H, s), 7.74 (1H, d, J=8.6 Hz), 7.82-7.97 (3H, m), 8.05 (1H, d, J=8.6 Hz), 8.58 (1H, s).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. customThe reaction was quenched with water (100 ml)
  3. extractionextracted with ethyl acetate-hexane (1:2)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by silica gel column chromatography
  7. washeluting with ethyl acetate-hexane (0:100 to 1:20)

Sources & evidence

ORD record
ord-3225ba91295742159b9f788d1a84d467
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

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