Hydrochloric Acid → HCID 118113253, compound

HRID 1485067Notes

Reaction equation

HRID 1485067 reaction equation
[CH3:1][C:2]([CH3:19])([CH3:18])[CH2:3][O:4][CH2:5][C:6]1[CH:17]=[CH:16][C:9]([C:10](N(OC)C)=[O:11])=[CH:8][CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[CH3:1][C:2]([CH3:19])([CH3:18])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH:10]=[O:11])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 21225700DiisobutylaluminumhydrideHCID 118113262HCID 118113262, compound

Product 1

HCID 118113253HCID 118113253, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution in tetrahydrofuran (5.93 mL) of the compound (472 mg) obtained in step (2) above, diisobutylaluminum hydride (about 1.0 mol/L, solution in n-hexane, 2.64 mL) was added at −78° C. After stirring the mixture at −78° C. for 30 minutes, 1 mol/L hydrochloric acid (5.00 mL) was added at that temperature. After being stirred at room temperature for an hour, the reaction mixture was poured into 1 mol/L hydrochloric acid (20.0 mL). After three extractions with ethyl acetate, the combined organic layers were washed with saturated brine. The washed organic layers were passed through a phase separator and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-90:10) to give the titled compound as a colorless oil (302 mg).

Workup

  1. stirringAfter being stirred at room temperature for an hour
  2. extractionAfter three extractions with ethyl acetate
  3. washthe combined organic layers were washed with saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-90:10)

Sources & evidence

ORD record
ord-08c339f1db9c4574a45757f29e11be21
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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