Water → HCID 86593287, compound

HRID 1610652Notes

Reaction equation

HRID 1610652 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:29])[CH:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.O>C(OCC)C.[Cl-].[Zn+2].[Cl-]>[C:25]([O:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][CH:11]([CH:10]([C:7]1[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=1)[OH:29])[C:12]([O:14][CH2:15][CH3:16])=[O:13])([CH3:26])([CH3:27])[CH3:28]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22261696HCID 22261696, compound

Product 1

HCID 86593287HCID 86593287, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of anhydrous zinc chloride (8.17 g, 60 mmol) in diethyl ether (100 ml) was added sodium borohydride (4.54 g, 120 mmol) by small portions, and the mixture was stirred for 2 hrs. Insoluble material was filtered off and washed with diethyl ether. The filtrate was ice-cooled, and a solution of ethyl 3-(4-fluorophenyl)-2-[3-(tert-butyloxy)benzyl]-3-oxopropanoate (10.8 g, 30 mmol) in diethyl ether (20 ml) was added. The mixture was stirred at room temperature for 1 hr., ice-cooled again and water was added to stop the reaction. The mixture was washed with 5% aqueous potassium hydrogen sulfate solution and water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to give the objective substance (8.9 g, 79%) as a colorless oil. IR ν maxNeatcm−1: 1728, 1605, 1510, 1260, 1225, 1179, 1154. 1H-NMR (CDCl3) δ: 0.93(3H, t, J=7.2 Hz), 1.31(9H, s, But), 2.90-3.05(3H, m), 3.87(2H, d, J=7.2 Hz), 4.95-5.10(1H, m), 6.70-6.80(1H, m), 6.80(1H, d, J=7.8 Hz), 7.00-7.20(3H, m), 7.30-7.45(2H, m).

Workup

  1. filtrationInsoluble material was filtered off
  2. washwashed with diethyl ether
  3. temperaturecooled
  4. stirringThe mixture was stirred at room temperature for 1 hr
  5. temperature, ice-cooled again
  6. customthe reaction
  7. washThe mixture was washed with 5% aqueous potassium hydrogen sulfate solution and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated under reduced pressure
  10. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1)
  11. customto give the objective substance (8.9 g, 79%) as a colorless oil

Sources & evidence

ORD record
ord-a0f1394a9b5e4c849f8ea2477186ca56
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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