Acetic Acid → HCID 59191413, compound

HRID 1023993Notes

Reaction equation

HRID 1023993 reaction equation
[BH4-].[Na+].[CH2:3]([C:5]1[CH:23]=[CH:22][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:21])[CH2:17][CH2:18][CH:19]=[O:20])=[CH:12][CH:11]=2)=[C:7]([OH:24])[CH:6]=1)[CH3:4].C(O)(=O)C>CO.O>[CH2:3]([C:5]1[CH:23]=[CH:22][C:8]([O:9][C:10]2[CH:11]=[CH:12][C:13]([C:16](=[O:21])[CH2:17][CH2:18][CH2:19][OH:20])=[CH:14][CH:15]=2)=[C:7]([OH:24])[CH:6]=1)[CH3:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 59191234HCID 59191234, compound

Product 1

HCID 59191413HCID 59191413, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

To a suspension of NaBH4 (0.052 mmol; 2 mg) in dry methanol, under argon at −78° C., (0.5 mL) was added 4-[4-(4-ethyl-2-hydroxyphenoxy)phenyl]-4-oxobutanal (0.040 mmol; 12 mg). The reaction was stirred 5 hours with gradual warming to −5° C., and treated with acetic acid. The mixture was diluted with water and extracted with ethyl acetate. Combined organic layers were dried over Na2SO4 and concentrated in vacuo. The title compound was obtained as a clear oil (7.6 mg; 63%) after purification on preparative TLC (cyclohexane/ethyl acetate: 5/5).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialCombined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-786a01def1dc4aae99f3f85a6eb8dbbe
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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