Dimethylformamide → HCID 58497917, compound

HRID 1505263Notes

Reaction equation

HRID 1505263 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:17]2[C:12](=[C:13](Br)[CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CN(C)[CH:26]=[O:27]>O1CCCC1>[C:1]([O:5][C:6]([C:8]1[C:17]2[C:12](=[C:13]([CH:26]=[O:27])[CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14807709HCID 14807709, compoundHCID 178418339Butyllithium

Product 1

HCID 58497917HCID 58497917, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-95 °C

Procedure

To a solution of 5-bromo-1-naphtoic acid tert-butyl ester (Example 9.2) (6.1 g) in dry tetrahydrofuran (54 ml) cooled to −100° C. was added a solution of butyl lithium (1.6M in hexane) (12.5 ml) dropwise at −100° C., followed by addition of dimethyl-formamide (“DMF”) (2.77 ml) at −100° C. The reaction mixture was stirred at −95° C. for 75 minutes. The reaction was quenched by addition of aqueous ammonium chloride (saturated) (8 ml) at −90° C. The mixture was stirred for 10 minutes at −90° C., warmed to 0° C. and poured onto a mixture of ice and water. The mixture was allowed to warm to ambient temperature and then extracted twice with ethyl acetate. The combined organic extracts were washed with water, dried over sodium sulfate and concentrated to give 5-formyl-1-naphtoic acid tert-butyl ester (3 g) as yellow oil. 1H-NMR (CDCl3, 400 MHz): 10.35 (s, 1H), 9.50 (s, 1H), 9.18 (d, 1H), 8.15 (d, 1H), 8.00 (d, 1H), 7.65-7.75 (m, 2H), 1.65 (s, 9H).

Workup

  1. customThe reaction was quenched by addition of aqueous ammonium chloride (saturated) (8 ml) at −90° C
  2. stirringThe mixture was stirred for 10 minutes at −90° C.
  3. temperaturewarmed to 0° C.
  4. additionpoured onto a mixture of ice and water
  5. temperatureto warm to ambient temperature
  6. extractionextracted twice with ethyl acetate
  7. washThe combined organic extracts were washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b4481c17ae6a476186e0bd3a986bdb69
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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