Water → HCID 5368479, compound

HRID 1497010Notes

Reaction equation

HRID 1497010 reaction equation
[H-].[Na+].[C:3]1([CH2:9][CH2:10][CH:11]=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH2:13].[CH2:14]1[CH2:18][O:17][CH2:16][CH2:15]1.O>O1CCCC1>[C:3]1([CH2:9][CH2:10]/[CH:11]=[CH:15]/[C:16]([O:17][CH2:18][CH3:14])=[O:13])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7707BenzenepropanalHCID 24758Sodium hydrideHCID 21881883Oxolane--water (1/1)

Product 1

HCID 5368479HCID 5368479, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% wt., 181 mg) was suspended in dry tetrahydrofuran (5 ml) and cooled to 0° C. Triethyl phosphonoacetate (896 μl) was added dropwise. The reaction mixture was stirred at 0° C. for 30 min. After cooling to −78° C. 3-phenylpropionaldehyde (500 μl) was added dropwise. The reaction mixture was stirred at this temperature for 1 h. The reaction mixture was allowed to warm-up to room temperature, hydrolyzed with water/THF, poured into water and the aqueous layer was extracted twice with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated. The crude was purified by flash column chromatography.

Workup

  1. temperatureAfter cooling to −78° C
  2. stirringThe reaction mixture was stirred at this temperature for 1 h
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude was purified by flash column chromatography

Sources & evidence

ORD record
ord-123d6c269f1f45238ed9bcfd87f8b7ef
Source dataset
uspto-grants-2015_12
Patent number
US09199948B2

Reaction notes

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