Acetic Acid → HCID 59191413, compound

HRID 626083Notes

Reaction equation

HRID 626083 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-2dce8470ccca4c29a2af223e8a38eeb4
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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