1-Naphthaldehyde → HCID 11264629, compound

HRID 1275630Notes

Reaction equation

HRID 1275630 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Br-].[CH2:8]([O:10][C:11]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:12])[CH3:9].[C:32]1([CH:42]=O)[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1>O1CCCC1>[C:32]1([C:42](=[CH2:1])[C:11]([O:10][CH2:8][CH3:9])=[O:12])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 61951-NaphthaldehydeHCID 18366765HCID 18366765, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11264629HCID 11264629, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

220 ml of a 1 N solution of potassium tert-butoxide in tetrahydrofuran are added dropwise to a solution of 0.219 mol of ethoxycarbonyltriphenylphosphonium bromide in 200 ml of tetrahydrofuran. The medium is stirred for 1 h at room temperature, after which a solution of 0.22 mol of naphthalene-1-carboxaldehyde in tetrahydrofuran is added dropwise. The medium is stirred for 4 h at room temperature, filtered, the solvent is evaporated off and the residue is taken up in 400 ml of methylene chloride. The organic phase is washed with 100 ml of water, dried and concentrated. The residue is taken up in diisopropyl ether, the precipitate is filtered off and the expected product is obtained after concentration of the solvent.

Workup

  1. stirringThe medium is stirred for 4 h at room temperature
  2. filtrationfiltered
  3. customthe solvent is evaporated off
  4. washThe organic phase is washed with 100 ml of water
  5. customdried
  6. concentrationconcentrated
  7. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-6ba53c8e27b54b4d83675993ddd85fb3
Source dataset
uspto-grants-2000_12
Patent number
US06162822

Reaction notes

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