2-Naphthalenecarboxaldehyde → HCID 21190815, compound

HRID 1068870Notes

Reaction equation

HRID 1068870 reaction equation
C([Li])CCC.[CH3:6][C:7]1([CH3:18])[CH2:11][O:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8]1.[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[CH:29]=[O:30]>O1CCCC1.C1(C(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:6][C:7]1([CH3:18])[CH2:11][O:10][C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[CH:29]([C:20]2[CH:21]=[CH:22][C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:19]=2)[OH:30])=[N:8]1

Participants

6

Reactant 3

HCID 62012-NaphthalenecarboxaldehydeHCID 2892394,4-Dimethyl-2-phenyl-2-oxazolineHCID 178418339Butyllithium

Product 1

HCID 21190815HCID 21190815, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 10614TriphenylmethaneCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

At −78° C., 104 ml of a 1.6M solution of butyl lithium were slowly added dropwise to 25 g (0.14 mol) of 4,4-dimethyl-2-phenyl-2-oxazolin and 0.1 g of triphenylmethane in 400 ml of anhydrous tetrahydrofuran. The mixture was stirred for 1 h. The mixture was then allowed to warm to −30° C. and a solution of 20.3 g (0.13 mol) of 2-naphthaldehyde in 200 ml of anhydrous tetrahydrofuran was added dropwise. Stirring was continued for about 1 h at −20 to −30° C. The reaction solution was then allowed to warm to room temperature and the solvent was removed under reduced pressure. The residue was introduced into ice-water which was then extracted with ether. The organic phase was dried and concentrated under reduced pressure. This residue was purified chromatographically (eluent: n-heptane/acetone=40/3), affording 25.3 g (54%) of the product.

Workup

  1. stirringStirring
  2. waitwas continued for about 1 h at −20 to −30° C
  3. temperatureto warm to room temperature
  4. customthe solvent was removed under reduced pressure
  5. additionThe residue was introduced into ice-water which
  6. extractionwas then extracted with ether
  7. customThe organic phase was dried
  8. concentrationconcentrated under reduced pressure
  9. customThis residue was purified chromatographically (eluent: n-heptane/acetone=40/3)

Sources & evidence

ORD record
ord-5f3d605609224ab8bd0fc0b6b0d9c20e
Source dataset
uspto-grants-2001_06
Patent number
US06251917B1

Reaction notes

Loading…