Hydrochloric Acid → HCID 53773709, compound

HRID 374681Notes

Reaction equation

HRID 374681 reaction equation
[Cl-].[Li+].C(OP([CH:11]([CH2:17][CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.C1CCN2C(=NCCC2)CC1.[C:38]1([CH:48]=O)[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1.Cl>C1COCC1>[C:38]1([CH:48]=[C:11]([CH2:17][CH2:18][CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 61951-NaphthaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 14649483HCID 14649483, compound

Product 1

HCID 53773709HCID 53773709, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

579 mg of lithium chloride was suspended in 20 ml of dry THF under an argon stream, and 5.0 g of ethyl 2-diethylphosphono-5-(2-tetrahydropyranyloxy)pentanoate was added under stirring. After stirring the mixture for 5 minutes at room temperature, 2.6 g of DBU was added, and the mixture was stirred at room temperature for 10 minutes. Then, 1.7 g of α-naphthoaldehyde was added, and the mixture was stirred at room temperature overnight. Then, the reaction solution was neutralized with 1N hydrochloric acid under cooling with ice and extracted with ethyl acetate. The ethyl acetate layer thereby obtained was washed with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) to obtain 3.37 g of ethyl 3-(1-naphthyl)-2-[3-(2-tetrahydropyranyloxy)propyl]-2-propenoate as slightly yellow oily substance.

Workup

  1. additionwas added
  2. stirringAfter stirring the mixture for 5 minutes at room temperature
  3. stirringthe mixture was stirred at room temperature for 10 minutes
  4. stirringthe mixture was stirred at room temperature overnight
  5. temperatureunder cooling with ice
  6. extractionextracted with ethyl acetate
  7. customThe ethyl acetate layer thereby obtained
  8. washwas washed with water and with a saturated sodium chloride aqueous solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-f47dca8090724d97a342856c98189847
Source dataset
uspto-grants-1996_01
Patent number
US05481036

Reaction notes

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