Hydrochloric Acid → HCID 67146913, compound

HRID 2422217Notes

Reaction equation

HRID 2422217 reaction equation
[O:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[CH2:2]1.[BH4-].[Na+].Cl.O[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(O)C.[Cl-].[Na+].O.O.O1CCCC1>[O:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[CH:3]([O:10][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:17][CH:16]=2)[CH2:2]1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 23556CoumaranoneHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 4311764Sodium borohydride

Product 1

HCID 67146913HCID 67146913, compoundYield 17%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3-coumaranone (0.50 g, 3.7 mmol) in ethanol (20 mL) was added sodium tetrahydroborate (0.28 g, 7.5 mmol), and the mixture was stirred at room temperature for 1 hr. 0.5N Hydrochloric acid (10 mL) was added and the mixture was stirred at room temperature for 10 min. Saturated brine was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated. Tetrahydrofuran (10 mL), methyl 4-hydroxybenzenepropanoate (0.46 g, 2.6 mmol), triphenylphosphine (0.98 g, 3.8 mmol) and diethyl azodicarboxylate (0.91 mL, 4.7 mmol) were added to the residue, and the mixture was stirred at room temperature for 2 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20:1) to give the title compound. yield 17%, oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. stirringthe mixture was stirred at room temperature for 2 hrs
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with water
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-7683915565864add96e3fa3ad3c7c000
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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