Water → HCID 86691236, compound

HRID 2038220Notes

Reaction equation

HRID 2038220 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH:7]([C:13](OCC)=[O:14])[C:8](OCC)=[O:9])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH2:13][OH:14])[CH2:8][OH:9])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 86691237HCID 86691237, compound

Product 1

HCID 86691236HCID 86691236, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve diethyl 2-(4-fluorophenoxy)propanedioate (360 mg, 1.33 mmol) in THF (10 mL); slowly add lithium aluminum hydride (1.0 M in THF; 3.6 mL, 3.6 mmol); and stir at ambient temperature for 30 minutes. Quench reaction via the addition of H2O (1 mL) and extract with EtOAc. Dry the organic phase over Na2SO4. Filter and concentrate the filtrate under reduced pressure. Purify the resulting material via silica gel flash column chromatography (12 g), using a gradient of 10%-50% of EtOAc in petroleum ether. Concentrate the desired fractions under reduced pressure to give the title compound as a colorless oil (195 mg, 78.6%). 1H NMR (300 MHz, CDCl3) δ 7.0 (m, 4H), 4.3 (m, 1H), 3.9 (m, 4H), 2.4 (bs, 2H).

Workup

  1. customQuench
  2. customreaction
  3. extractionextract with EtOAc
  4. dry with materialDry the organic phase over Na2SO4
  5. filtrationFilter
  6. concentrationconcentrate the filtrate under reduced pressure
  7. customPurify the resulting material via silica gel flash column chromatography (12 g)
  8. concentrationConcentrate the desired fractions under reduced pressure

Sources & evidence

ORD record
ord-461f5178f46f4b87bcd44e14a13cc4ef
Source dataset
uspto-grants-2013_11
Patent number
US08575352B2

Reaction notes

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