Ethyl Acetate → HCID 69143601, compound

HRID 1766861Notes

Reaction equation

HRID 1766861 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:24]=[CH:23][C:8]([CH2:9][O:10][C:11](=[O:22])[CH2:12][CH2:13][C:14](=[O:21])[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])=[CH:7][CH:6]=1.[Cl-].[NH4+].C(OCC)(=O)C>O1CCCC1.[Cl-].[Zn+2].[Cl-].CCCCCC>[OH:21][CH:14]([CH2:13][CH2:12][C:11]([O:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:24][CH:23]=1)=[O:22])[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 58885353HCID 58885353, compound

Product 1

HCID 69143601HCID 69143601, compoundYield 68.1%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

Zinc chloride (1.0 M diethyl ether solution; 8.8 ml, 8.8 mmol) was added to tetrahydrofuran (5 ml), and sodium borohydride (605.3 mg, 16.0 mmol) was added thereto with stirring at 0° C. The mixture was irradiated with ultrasonic waves for 10 minutes using a commercially available ultrasonic cleaner. The mixture was taken out of the ultrasonic cleaner and cooled to −5° C., and a solution of allyl 5-[(4-methoxybenzyl)oxy]-2,5-dioxopentanoate (1.84 g, 6.0 mmol) obtained from Example 2-(1) in tetrahydrofuran (5 ml) was added thereto over a period of 10 minutes. The resulting mixture was stirred for 30 minutes, and then a saturated aqueous solution of ammonium chloride was added thereto to stop the reaction followed by extraction of the product with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure to afford an oily residue. The residue was subjected to chromatography on a silica gel (65 g) column (eluent; ethyl acetate:hexane=3:10˜2:5) to afford the title compound (1.26 g, 68% yield) as a colorless oil.

Workup

  1. additionwas added
  2. customThe mixture was irradiated with ultrasonic waves for 10 minutes
  3. temperaturecooled to −5° C.
  4. stirringThe resulting mixture was stirred for 30 minutes
  5. extractionfollowed by extraction of the product with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto afford an oily residue

Sources & evidence

ORD record
ord-88b1e595275a4dd8ae9e068855586ff8
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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