Acetic Acid → HCID 58828974, compound

HRID 1171449Notes

Reaction equation

HRID 1171449 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([O:10][CH2:11][CH2:12][CH3:13])[CH:3]=1.[C:14]([OH:17])(=O)[CH3:15].[C:18]([BH3-])#[N:19].[Na+].O.CN(C)[CH:25]=[O:26]>>[CH2:14]([O:17][C:25](=[O:26])[CH2:6][C:5]1[CH:8]=[CH:9][C:18]([NH:19][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([I:1])=[CH:3][C:4]=2[O:10][CH2:11][CH2:12][CH3:13])=[CH:3][CH:4]=1)[CH3:15]

Participants

6

Reactant 5

HCID 176Acetic Acid2×HCID 962WaterHCID 6228Dimethylformamide2×HCID 5003444Sodium cyanoborohydrideHCID 86054523HCID 86054523, compound

Product 1

HCID 58828974HCID 58828974, compoundYield 85%

Procedure

1.50 g (5.17 mmol, 1 eq) of 4-iodo-2-propoxybenzaldehyde in solution in 40 ml of dimethylformamide supplemented with 1% of acetic acid is added to a solution in 40 ml of dimethylformamide supplemented with 1% of acetic acid. The reaction mixture is stirred overnight at room temperature. 50 g (5.17 mmol, 1 eq) of sodium cyanoborohydride are added. The reaction medium is heated at 60° C. for 4 hours. After returning to room temperature, the reaction medium is supplemented with water and then extracted with ether. The organic phase is dried over magnesium sulfate, filtered and then concentrated. The residue is chromatographed on silica gel (heptane/ethyl acetate 80/20). 2.00 g (85%) of the expected compound are obtained.

Workup

  1. temperatureThe reaction medium is heated at 60° C. for 4 hours
  2. customAfter returning to room temperature
  3. extractionextracted with ether
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (heptane/ethyl acetate 80/20)

Sources & evidence

ORD record
ord-803221d114d748df97e2565fb47e56db
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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